Tony Hawk's Pro Skater 1 + 2

Pretty sure I was world first on all platforms for this, pretty stoked about that.

You can find the list for these under Challenges>Skate Park Challenges> THPS1 Get-Theres/THPS2 Get-Theres. They all have specific names, I just went level by level. You can read the description of them and it will tell you the specific level. These are all the ones labeled "Hard".

EDIT: NOVEMBER 2020 UPDATE: Roswell is now LOW DECK, not high deck. My video is now excessive and wrong.

Edit: I'm removing all the separate videos because it's causing the page to be awful to open.

Here's the a youtube video compiling all of them.

THPS1

00:04 Warehouse - Oh, Holy Pipe
00:20 School - Uphill Both Ways
01:06 Mall - Stairway Down
02:16 Skatepark - Windy Walkway
02:39 Downtown - Down and Around
02:56 Downhill Jam - Teleporter? What?
03:19 Burnside - Rollin' The Hill
03:33 Streets - Spiral Fountain
03:56 Roswell - Rollin' Deck (Old - see edit)

THPS2

04:26 Hanger - Corner Hopper
04:44 School II - Railing Kill
05:25 Marseille - Tour The Riviera
05:45 New York City - Snack Time
06:08 Venice Beach - From the Roof!
06:24 Skatestreet - Surfin' In the Pool
06:45 Philadelphia - Flyin' Wheelie
07:16 Bullring - Banana Bandana
07:50 Chopper Drop - Go! All! The! Way!
08:06 Skate Heaven - Intersectional

General tips:
These guys are basically centered on your ability to control your speed, and manual/grind bars, and minutely adjust your character to proceed to the next gaps. I hope y'all don't have to spend remotely as much time on them as I did, as you now have a basically line to abide/morph. I spent about 6 hours on Bull Ring alone. I'm talking thousands of attempts across all these guys. With probably 60 percent of my time spent on Roswell and Bull Ring.
Be patient. Don't be afraid to work on a single section of the combo, or work your way from the end to the beginning (As in, completing the last gap alone, then doing the last again and the second to last, etc) I worked backwards through a LOT of these to make sure I wasn't going to flub the ends after having the middle/beginning be a pain.
If you're not actively changing your character's direction, or getting ready for a gap/jump/whatever, be comboing. Grinds increase your speed, which will help if you need to revert/go uphill. Spamming flip tricks will help you spend less time manipulating your balance.
You basically always want to have full special when starting these. You have a higher top speed, higher ollie height, and longer air time with full special. It will be fully utilized. The only exception to this is my route on Bull Ring, which i'll explain in that section.
I recommend getting used to the d-pad. The thumbstick can input even minute directional inputs that can wreck a manual/grind easily.

On a few of these there will be multiple videos. This is because I realized more efficient ways of combining the gaps. I have cheats on in a few of these because I was searching for gaps I was missing, but they're typically easier than the way I did it. Having said that, these will have multiple ways of completing them, if you feel like you have a better shot another way, take it. On the majority of these levels, I tried 3 or 4 different routes before picking the one I was going to focus on.

I'll be going in order of levels, starting with Warehouse in THPS1.
Anyway, lets go.

Warehouse:

You need to get two gaps in this, Over the pipe, pretty self explanatory, jump over the half pipe, and then the Holy Shi.... gap. This one is for grinding the entire backwall quarter pipe. Not much to say here. You have to go pipe first, then grind, because the reverse has you hitting your head on the secret room.

School:

First clip is how I first landed it, second is pretty definitively the easier way.

You need 6 gaps in this, but they're pretty well set up.
In the order I did them,
Garbage ollie: Jump over the dumpster in the back of the gymnasium.
Dumpster Rail Gap: Jump from one rail to the other, over the garbage on the side of the gymnasium.

Straightforward so far, these line up with a curved dumpster grind between them.

2x Planter gaps: Jump from one planter to another in a continued grind just under the starting point. In the two videos you can see the two separate ways to approach this. One is to just head straight at the most direct planter after the Dumpster Rail gap, and then you'll end up a bit long on the turn to head down the big stair case, but its manageable. The other is to go wide after the Dumpster Rail gap, and it lets you line up very well to get the Rail to Rail Transfer. This is seen in the second video.

Rail to Rail transfer: Two locations for this that work well, one is seen in the first, its a small jump, little speed required, problem lies in how far it is. You need to stretch your combo pretty solidly to reach the location, which is at the far side of the open area at the bottom of the large stairs. This was how I did it initially because I thought the gap was limited to certain areas, but I was wrong, hence why I redid it the second way, which is on the large staircase jump from the railing that gives the All-Access Pass gap, onto the planter running parallel with it. Then you can proceed easily to:

Kicker gap: Jump between the kickers at the bottom of the main staircase. Simple.

Onwards to the MALL:
This one shows me doing it a second time, with cheats on, because the first time I didn't know the final gap, Over A Huge Stair Set, could be acquired with a wallride, so I started at the end, and teleported to the beginning and combo'd my way back down, because its basically impossible to flat out jump the 32 set with your reduced speed from the combo. This way is very straight forward.
Gaps: Over a Stair Set, Skater Escalator Gap, Over a Huge Stair Set

First gap is the Over a Stair Set: 16 set after the Coffee Grind rail under the giant leap from the 3rd balcony area. Easy start, speed isn't very necessary as you'll be grinding a ton, building it back up.

Keep going straight to the Skater Escalator Gap: again, easy, you've got great rails leading up the this to put you on an easy line to jump it, and rails following to get your speed back up.

The atrium before the stair set is the difficult part, there are many ramps that you can accidentally land on killing your speed, so I just grind the ledge on the walls (For the whole atrium! gap).
You HAVE TO JUMP FROM THE BOTTOM FLOOR of the split level of the big staircase. The top is a SEPARATE gap. (Huge Stair Set off a Mezzanine)
Hit a long wallride, and wallie once you're close to the ground. You'll see in my video I hit the wall on the far side, that's just fine as long as you don't wreck.

Okay, SKATE PARK. This dude was a bit troublesome finding a line for, and I'm still not sure what the triggers are for the pool grind, but this line is pretty simple.
Gaps: Walkway Rail Transfer, Over the Box, Wall gap Jr., Around the Bend, HP Transfer

Starting from the walkway behind the spawn point: Walkway Rail Transfer. Jumping from the walkway, onto one of the two parallel green rails on the fun boxes. You need special to hit this cleanly, otherwise its a pain. make sure you come off the rail straight.

Over the box: Jump over the mixed fun box next to the half pipe.
You can hit the edge of this, just need to clear it, but you can get a little pop from it. You can do what I did, which is straighten out with a revert on the quarter pipe next to it, or you can just line yourself up. Whichever you prefer, regardless, the further away from the halfpipe you can be pointing when you land, the better.

Wall gap Jr.: Jump over the smaller half of the small wall that's right in front of you when you spawn. Super easy. In your jump, line up your grind on the pool, which will be on the right edge, around the back, until you're lined up to the half pipe,
hopefully popping the:

Around the Bend Gap: This circles the pool, opposite the indented side. I can't tell if its supposed to be the hip itself, but I couldn't find a good angle to run it that way even if it was, so I just went the other way.

Finally, HP Transfer: Jump from the small quarter pipe right in front of you at the spawn, into the half pipe.
Find a good angle after coming off the pool jump, which your speed shouldn't be too bad, you may be able to fit a grind reset on the back half and still pop the gap, but I didn't need to, and hop over. Pretty easy little jump, just make sure you're aligned right coming into the pipe so you won't crash.

DOWNTOWN:
This guy is fun, because you can really hit it at any point in the route you can see me take. I was basically making a circle for about 20 minutes, trying it again whenever I bailed until I made it. I'll list them in the most logical way though, which was the original intention of the combo. Be wary of the cars, and your speed when going to the Deck Gap.
Gaps: Kicker Gap, Kicker 2 Street, Car Ollie, Cheesy Deck Gap

Kicker Gap: starting from your spawn, you jump from one kicker to the next right in front of you. For our sake, we're going to be doing it the opposite way, because we
need it to lead to:

Kicker 2 Street: Using one of the two parallel kickers right behind the spawn point, launch to the street behind you, heading to the right as best you can, and avoiding the crazy taxi drivers swirling around. You can head to either side of the ramp at the top right corner, depending on when you want to hit the Car Ollie, because there's one on the left side of the street, or on the other side of the Cheesy Deck Gap, there's another car easily used. Your choice.

Car Ollie: Ollie over a parked car. There are two that line up for this, on opposite sides of the road, on opposite sides of the Cheesy Deck Gap. Pick your poison and ollie it. You won't see the one I mentioned above in this video, as that section of the street wasn't used in my combo.

Cheesy Deck Gap: launch over the small side of the large triangular deck further down the street. You can also grind the edge from the other end, and jump diagonally across it, but it can be finicky, so find the boundaries of it if you're planning on doing it that way. I was using that way as well sometimes.

Now, DOWNHILL JAM. This was the first one I really got frustrated with. It is a pain. You need to manual into a jump over the center pipe fixture, and land, manually, through the tiny little gap, and launch out of it. So I figured out a way to have to make it be the least big a problem: I put it at the end of the combo, rather than in the middle of it. Then, I only had to get it right ONCE.
Gaps: The Downhill Halfpipe, The Other Downhill Halfpipe, 50 Feet

This first section will cover The Downhill Halfpipe gap and The Other Downhill Halfpipe gap.

Immediately, you'll notice I'm going uphill (I honestly don't even remember if you could do this in THPS 1, and was this level always so short? It felt like miles to me when I used to play it.) This game gives you speed when you start a grind, and you can abuse this like you see me do it. Be noted: These two grinds down (up) each side of the halfpipe are FINNICKY going backwards, because their trigger areas are at the VERY. END. of the halfpipe. So, you have to start your grind at the very end of the halfpipe. I tried this probably 150 or 200 times total (the whole shebang).
land your manual facing as far away from the wall as you can without wrecking, gauge your speed. You can wallride into the grind on the left (facing down the level) side of the halfpipe, just make sure you don't wallride too far.

Once you've cleared both sides, this is the obnoxious part.
50 feet:
You need to quickly and cleanly line yourself up as dead center on the big pipe figure on the far side of the hole in the center of the level, as you need to jump over it, and land in the far side tunnel, to launch into the 50 feet gap (Part of the 25,50,75,100,125 chain). There's not a ton of help I can give you here. Be patient. It's a super tiny window you're trying to hit. Just don't try to grind the edges. It always just pushed me out when I tried, never roped me in. You don't need a huge amount of speed, if your line is good. The quicker you hit the ground the more you can control yourself, but then you've got to balance, so its a catch-22. Good luck. Stay strong.

BURNSIDE:
This was the first one I did, as it was the first in order in the game. It's a fun one, pretty excited I started with it. The competition levels tend to be fairly straightforward, as there's not as much room to work with. The only real trouble is found in jumping from the second to third rail in the triple rail gap. I would practice this a bit until you're comfortable, or else you'll spend a lot of time doing the rest of the gap.
Gaps: Bottom Shelf Lip, Rollin' The Hill, Triple Rail

Fairly straight forward, just a few notes.

Bottom Shelf Lip: I hate lip tricks, they're so finicky. You need to do a lip trick on the lower edge of the far blue wall. Line it up in the middle with the little bump in the center, as that's the next gap. If you feel like you may need a bit more speed, do a board stall of some kind (where your character is standing on the board on the lip), and you can ollie out to come out a bit faster, but not by much. Drop down, revert, manual and hold it over the little hill to pop:

Rollin' the Hill: manual over the small hill in the center, near the back pool.
Head straight over it towards the spawn/edge of the eye pool. Be careful jumping over the colored flooring here, as its actually a bit of a ledge on the far side, and you can drop your manual very easily. If you think you're gonna clip it, either input another manual, or jump again. Line yourself up with front, very right edge, of the spawn chute, as you can grind it around, leading to the triple rails easily.

Triple Rail: You need to grind in succession all three of the orange planters on the left side of the spawn. The last jump, from the second to third, is frustrating at best. You can't jump too early from the second rail, or the gap won't trigger, but if you jump to late you won't make it. Annoying, but not too awful. Just takes some getting used too. Speed can be a killer here, so you don't need to be flying through this part.

STREETS:
This guy is really straight forward, I think it took me like 2 or 3 tries. The line is simple, you've got tons of stuff to grind to keep speed up, and lots of room to combo so you're not in a long manual, plus the gaps are super simple.
Gaps: Backwoods Ledge, Down the Spiral, Rail 2 Rail, Around the Fountain

We start at the opposite side of the map from the spawn, near the spiral ramp in the corner. The first gap is to the right of that, if you're looking directly at it, at the big tree planter.
Backwoods Ledge: Launch off the right side of the tree planter (Wallride works best) and grind along the ledge behind it, into the room at the top, through the window (It will naturally pop you up, just activate a manual when you land). Simple, don't ollie at the end, and aim for the closed door on the left side of the room that will open up when you land from the grind. Once through the door, grind the LEFT side of the walkway, holding it all the way down. If you're not good at grinding you'll find out now, as this is a decently long one.

Once at the end, stay to the right of the street, heading towards the railings ahead of you to work on Rail 2 Rail gap.
Easy enough, grind one side, hop across, grind the other, and work your way towards the end of the loooong planter right in front of you. You'll need to wrap around the far end, to get to the end of the fountain that you need to grind around for

Around the Fountain: Only difficulty comes in either: very high speeds, or bad angle of approach. Come wide around the planter and give yourself a good point to start from and this one will be done quickly.

ROSWELL-If you can't launch past quarterpipes well, you're going to be here a while. See: Me. I'm awful at it. Took me like an hour and a half just to land the high deck gap twice and I got the entire rest of the combo on my second try without practice. It isn't hard. Its just annoying.
The big part of this is timing the release of your jumps on the quarter pipes. Time them early for more height, and late for a flatter angle. So aim high for a high wall jump off the invisible walls opposite the high deck, and aim low to get further distance to make the high deck gap.
You need to go: High Deck Gap, Roll-in channel gap, Grey Grind, and Roswell that Ends well for your gaps.

Not shown: Me going literally back and forth again and again over the center section hoping to land this stupid gap. Now it doesn't matter what side you land it on, as it will just change how you go about completing the combo, so focus on landing the High Deck Gap one way or the other. You need to Boneless AND time your launch to be as horizontal as possible. If you come super close, manual, because it activates just a tiny bit before the actual edge, so you can hit it
sometimes before you cross, and if you manual, you can move along. Anyway, two ways. If you land it going FROM the spawn TO the far side, then you're going to do what I do, and just head into ROSWELL THAT ENDS WELL, which is a manual from the bottom of the alien's hallway to the top, which is where GREY GRIND is. You must grind all three of the separate rails leading from corner, to corner, back to the spawn, and finally, head up the ramp and grind the half pipe, jumping across the starting roll-in for ROLL-IN CHANNEL GAP.

The other way, if you land FROM the far side going TO the spawn, then hopefully you were placed on the side I was, (right hand side of the spawn, if you're standing in it, looking across the level) so you can immediately go into a grind to jump across the ROLL-IN CHANNEL GAP, and wrap around the far edge, and jump across the secret pool doorway, and then manual your way down to, and through the hallway for ROSWELL THAT ENDS WELL, and then across the 3 rails for GREY GRIND. This CAN'T be done the opposite way. I had neither one activate after multiple tries trying to go from the end of grey grind, and a downhill manual.

Good luck. God be with you.

THE HANGER
You're hitting 4 gaps here, but its very simple, definitely one of the easier ones.
Gaps: Lil' Light Hopper, Big Light Hopper, Chopper Hop, Light Corner

Lil' Light Hopper: Jump from the half pipe in the main room, to one of the two long overhanging light bars on either side of it. Pretty straight forward, just get speed on the other side of the pipe, and launch forward out.

Big Light Hopper: This is for landing on the light bars on the other side of the glass wall in the center of the level, you'll get this naturally as you grind towards the far edge of the room from the Lil' Light Hopper gap, also acquiring:

Chopper Hop: For jumping across the glass wall into or out of the room with the chopper in it. It will pop when you jump from Lil' Light to Big Light.

Light Corner: Jump from the Big Light Hopper Light, onto the one perpendicular to it at the end. Jump watch your speed, should be straightforward.

SCHOOL II

Here's a big boy. I hope you've got your ballerina fingers on, because you've got some balancing to do. This one really becomes much easier if you can ollie quickly, so you can keep yourself out of a manual/grind as much as possible. Learn when the first roll call rail pops quickly, about half way down the final rail section, so you can give yourself a good line into the gym rail. Definitely focus on hitting the grinds after the 2nd roll call rail in the corner, or your speed will be way too low to manage the end effectively. This one will test your abilities if you've been challenged thus far.

I tried to hit these in a different order, but you really just leave yourself high and dry if you don't follow this path. Only remotely possible other way is to go for the 3rd roll call rail after the 1st, then do the gym gap, and finally the back corner roll call.
Don't recommend it though.

Roll Call Nightmare Rail!: Grind down the entire banister of the main staircase directly ahead of the start.
Easy start, just time your exit to be right after it pops, so you can align easily with the next gap. Be wary of the security cart, but he's usually out of your way if you just restart the round when you bail.

Gym Rail 2 Rail: Grind from one rail, jumping over to another, on the two rails in front of the gymnasium.
Simple gap, try to grind as little as possible, since the last gap is a decent grind, don't want to be fighting the balance bar. Get ready to go around the corner, but don't cut it too tight, there's a quarter pipe right there and bumping the wall will likely knock you out of a manual.

Roll Call Gonz Rail!: Grind the hand rail leading down the rear exit of the gym (typically by jumping off the kicker, but the quarterpipe works too).
I mainly late-ollied (releasing A to ollie after you've passed the end of a ramp) to hit this easily at speed. Then would exit right as soon as it popped to get ready to hit the red/white platform grinds to get my speed up going into the final section.

Roll Call Opensezmee Rail: Grind down the railing leading from the library to the main campus area.
If you're going slowly, you can wallplant earlier, before the lockers, but I always focused on keeping my speed up throughout, so the final grind is faster. If you've been focusing on keeping grinds short and sweet, your balance bar shouldn't be too wacky here. If you've made it this far, you can easily finish this get-there. I believe in you.

MARSEILLE

Couple notes: to hit the grind on the kink to kink black funbox, late-ollie (ollie after you've dropped off the rail) and immediately hit grind. You don't have to gap nearly as large as I did on the box2box action. You can just hop from one, onto the other, pretty easily. It just helps to make sure you don't lose speed. The final gap, the dumpster pop, MUST BE LONG WAYS. across the short dimension will give you "Shorty Dumpster Pop" which does not count for the challenge. You can get these on any of the dumpsters throughout the level, the one I chose just seems the most easily added to the line.

Gaps: Over the Table, Ledge to Rail, Rail to Rail, Box to Box Action, Dumpster Pop

Over the Table: Jump over the table that is sitting half in the pool.
Easy start, just make sure your attack angle will give you a good exit angle to approach the edge of the pool to head over to:

Ledge to Rail: Jump from the top of the staircase, grinding on the ledge, near the corner to the right of the start, to the curved rail in the corner of the level.
Just watch your exit, so you clear the small funbox so you don't lose speed.

Rail to Rail: Grind from one rail, and jump into a grind on the other on the quarterpipe funbox just behind the spawn.
As I mentioned above, time your ollie off the first rail to be after your exit from it, so you can immediately get into a grind on the second rail instead of jumping clear over it. I also don't recommend jumping to exit the second rail, as you will end up landing on the upslope of the box, killing your speed. Just fall into a manual.

Box to Box Action: Jump from one funbox to the other in front of the large wall.
You can just jump from the top of one, to the other, but I prefer wallriding over to not lose speed and to make sure I clear it easily. Just make sure you ollie to the wallride once you've started going up the first box, if you jump too early, you may not activate the gap.

Dumpster pop: Jump length-wise over a dumpster.
Final piece, just make sure it is on the long axis. Short axis, from experience, does not count.

NY CITY

Not a bad challenge here. Timing your jumps between the grinds in the park can be a bit annoying at first, but its just a matter of figuring it out. Make sure you hold you grind on the stand in between the benches and rails long enough to be able to activate the second gap there.

Gaps: Park Entrance Gap, You're Next In Line, Grab a Snack and Sit down, Joey's Sculpture

Note: If you do it exactly how I do, getting the "Burp, Now Go Skate!" gap, you should unlock a secret challenge. It gives you a badge of a weiner on a skewer.
Neat.

I tended to start this line on the bottom floor by the fountain in the park, coming up the bank, so I could have an easier time gapping off the Park Entrance wall, towards the railing.

Park Entrance Gap: Jump from one side of the stone wall to the other just to the left of the spawn. Simple stuff. Exit towards the rail by the lake. Not much to say.

You're Next In Line: Grind from the rail on the lake, jumping to the food service bar in the corner.
Watch your exit. Too late, you'll hit the building. Be ready to exit from the next grind shortly after landing.

Sit Down and Grab a Snack: Jump from the food service bar railing, to the benches alongside it. Just make sure you grind on the food service bar long enough for this to count. If you tap it, it may not register.

Joey's Sculpture: Grind down the sculpture in the lower plaza.

Easiest line imo is in my video, the grind follows around the corner, giving you a great exit point nearly right at the sculpture, just watch for taxis, and certain exit points can end up with you running into the support beams for the subway.

VENICE BEACH

This is a pain. Definitely gotta be precise with your speed control to get into the manual on the right spot, on a good line.
Gaps: Touchdown!, Ramp 2 Roof, Canyon Jump

Start with Ramp 2 Roof: Jump from the ramp located at the far end of the plaza you spawn looking at, onto the metal quarter pipe on the left This one is finicky, because if you do it really well, it gives you too much speed to easily turn around to make canyon jump. So you've got to find a short line that lets you exit towards Canyon Jump decently well.

Canyon Jump: Jump from the lower tier of the two-tier main roof, to the roof with the vent-ramp connected to the Ramp 2 Roof quarter pipe. You'll be jumping across the "Massive 20-stair!" staircase down into the alley.
You can get this to pop if you grind the edge of the upper tier and launch directly to the lower roof, negating having to drop to the lower tier after the Roof 2 Ramp Jump.

Touchdown!: This is a series of 3 gaps, Titled "He could go..., All the way...." "Touchdown!" for manualing the length of the boarded tables in the center of the plaza.
You need to be precise with where you land for this. You can't land very far onto the first table, and you need a good line when you land, because you won't have room to adjust enough at the speed you have to be going to get all the way across. I wouldn't hesitate to practice this a good bit so you can be confident after landing the previous segments.

SKATESTREET

This one is made easier by a bugged gap. "Circle the Pool" The way the gap triggers is if you are in a grind over one side of the extension, and in a grind on the other, it will pop it, as long as you exit away from the extension on the first go around. So you can get this to pop by grinding the extension towards the wall, ollieing late, so you are technically grinding while over the start of the lower edge of the pool, and jumping into the wall, wall planting, and grinding back across the extension, and dropping off it onto the pool edge. Then you just have to do a quick wall bounce instead of holding a grind around the whole pool.
The only annoying part for me was getting on top of the giant wave quarterpipe, and into the grind. Its difficult to get an angle directly onto the railing, so I ended up learned on the quarterpipe and just manualed over to the rail. Just can't go too far or the gap you need from the pipe won't activate.

Gaps needed: Circle the Pool, Extension Transfer, Surfin U.S.A., Rail Secret Key Area, Over the Wall

Circle The Pool/Extension Transfer: Grind from one side of the extension on the pool to the right of the spawn, all the way around it for Circle the Pool, grind on the pool extension, drop onto the pool, and grind it, for extension transfer. See the paragraph above for the explanation of how this works, but grind on the extension towards the back wall, ollie late, after dropping off the extension, and wall plant off the wall, grinding back across the extension, then dropping onto a grind on the pool edge, that will point you towards to wave wall, where you need to head next.

Surfin U.S.A.: Grind over the hump on the top of the wave quarterpipe on the far wall.
You won't have enough speed to get up the pipe in any manual, so you have to take the rail on the right up there, better to miss right than left, as you can manual to the rail on the top, versus launching yourself into tragedy.

Rail Secret Key Area: Grind the hanging bar at the end of the wave quarter pipe over the big deck/funbox area.
Simple stuff. Just be careful on your exit, you want to be aiming for the right side of the support pillar that is merged into the mini-quarter pipe on the ground in front of you.

Over the wall: Jump over the small wall separating the tiny mini-quarter pipe from the long mini-quarter pipe in front of the big half-pipe.
Easy stuff. You've got this far, this part is simple.

Philadelphia

This one isn't too bad really. Just gotta be able to grind up the final wire.
You can also start with the wire, and then jump down from the top level of the building and go to the telephone gap. I found this easier.

Gaps: Telephone Company Gap, Funbox Wheelie, Bench, Fly By Wire.

Telephone Company Gap: Jump from the second story building to the right of your spawn (you can get up here by jumping off the little ramp at the bottom of the stairs, pretty easily) onto the telephone wire, in a grind.
Starts off easy enough. On your exit, I tended to exit a little early, letting me set up my approach for the manual easier.

Funbox Manual: Manual across the center funbox (tough to figure out with these names).
Easy here, just one continuous manual. Make sure your speed is good, and angle towards the benches on the left for the next gap.

Bench Gap: Just hop on the bench/ledge setup in a grind and keep grinding along it. Don't even have to ollie really. Watch your exit so you don't kill your speed landing in a gap between the benches and ledges. Head towards the opposite side planter area on your exit, so we can get the final gap.

Fly by wire: Grind up the large wire crossing the center of the level.
You can grind multiple times here, its necessary to build up the speed, just make sure you start early, and stay in a single grind near the end, so it will register.

Fairly straightforward, not much to say about Philly.

The Bullring

This was my nemesis. Quite the monster. It requires a ton of precision on the second gap (Launch to Banana). The hard part of this level though for me was finding the line. I saved y'all that struggle. There are definitely a few other possibilities for this level, but I'm over it!
The end is obviously not the most optimal route, but I accidentally started a grind on the bull ring and saved it. I was trying to manual up the ramp and spin around to approach the Rail Plat gap that I ended up getting back to. Don't make that mistake.

Necessary gaps: Nailin' The Rail, Up to the Stands, Launch To Banana, Rail Plat

Nailin' The Rail/Up to the Stands Honestly not EXACTLY sure what the triggers are, but its something like Jump from the Halfpipe area, high in the air, and land in a grind. You can pop this a thounsand different ways, but the problem is they all need good speed that is difficult to get on this map mid-combo.
You'll start by spine transferring between the O and U in the birdhouse logo on the back left quarterpipe (from spawn) attached to the half pipe, and land in a grind on the wire running over the top. I RECOMMEND HAVING NO SPECIAL FOR THIS. You have a much better window to jump to the crossing wire. With special, you take off like a missile and have almost zero time to react to getting on the wire. Without special you can find a rhythm. After 3 grinds you're up to top speed and need to be paying attention for the drop onto the stands coming up. I would drop when about 2 feet of the ground after the ramp on the top stands came into view under my skater. Land far enough in so Up to the Stands pops. Immediate manual, ramp, revert, and figure out how the hell to jump to the banana. (Up to the stands is just jumping up to the second level in one of a million different ways)

Launch to Banana: This was probably the most difficult section for me along with Roswell high deck gap. You need to launch from the kicker ramp on one of the top levels onto the large off-yellow banana shaped quarter pipe thing. With a metal bar in your way. This was about feeling. Sometimes I made it going left of the bar, sometimes right, it depends on how you land on the ramp, which changes your angle of attack. Just know if you don't have solid speed, its not happening. For a while I did not think this was even possible mid combo.

Rail Plat: You need to grind up one rail and down the other, covering the platform just across to the left of you connected to the half pipe from spawn.
The rail we come up to has multiple problems for using it as our initial rail:
It is near impossible to reach directly from banana, and it is awful trying to jump into a manual at it, and be lined up okay. It is steep, killing our speed, and has no flat area on top allowing us to get enough speed back to jump across the platform (The other side does). So we go to the opposite rail. You can try to launch off the little quarter pipe side, and revert and come at, but it requires a ridiculous reaction time that the camera just doesn't give you good opportunity to do. If you can get into a grind on this thing, you can beat this combo. Its just a matter of effort. Keep starting new grinds to hop your way up. Just try to land your first grind on the top right at the very start of the flat part, so you can jump and start another new grind so we can get a boost to jump across and beat the silly get-there.

Chopper Drop

Super easy: The gaps needed are 70, 80 and 90. Just build up special, head up the far ramp, and boneless launch across to the 'end'.

Skateheaven

This one was fairly straightforward for me. Took me 2 tries. I may have been lucky though.
4 gaps. Northern Intersect Sad, Mid Intersect Sad, Southern Intersect Sad, and Southern Crossover Sad.

These gaps are hard to explain as Skate heaven, and this snake, is a mess of a level (That I love). If you go to the start of the snake in my clip, the first gap on the left in the wall is the Northern Intersect Sad. You need to go directly across it. The next gap on the left is the Mid Intersect Sad. You need to go directly across it. The next gap is Southern Intersect Sad. You can pop it staying on the left, but you need to be on the right to get the next gap. Southern Crossover Sad. Jump from the right wall to the left wall after the southern intersection.

This is just a quick, tight, grind test. I don't have much to say other than speed kills. Watch your exits.


Good luck y'all. If you need more explanation of any specific one, message me, I'll see what insight I can provide.

First off, shoutout and thanks to Kourageous XY who made the first, and very helpful solution for this achievement. My solution is not meant to be a replacement of that, but it is meant to complement it and offer a slightly different approach/route in the challenges. I uploaded videos of all 19 challenges and you can watch them either individually or in a playlist. Good luck and hope it helps!

Playlist with all 19 challenges in THPS 1 and THPS 2

https://bit.ly/3m1EgTK

THPS 1

Warehouse - Oh, Holy Pipe

School - Uphill Both Ways

Mall - Stairway Down

Skatepark - Windy Walkway

Downtown - Down and Around

Downhill Jam - Teleporter? What?

Burnside - Rollin' The Hill

Streets - Spiral Fountain

Roswell - Rollin' Deck

THPS 2

Hangar - Corner Hopper

School II - Railing Kill

Marseille - Tour The Riviera

NY City - Snack Time

Venice Beach - From the Roof!

Skatestreet - Surfin' In the Pool

Philadelphia - Flyin' Wheelie

Bullring - Banana Bandana

Chopper Drop - Go! All! The! Way!

Skate Heaven - Intersectional

Adding this post as a supplement to Kourageous XY and K4rn4ge's guides. Just some tips and tricks to try that I didn't see either of them mention for the 3 hardest "Got There" challenges (In my opinion). If you're having a hard time with any of the challenges feel free to post/shoot a message my way with questions.

#1 General tip: HAVE PATIENCE. I know, I know, this isn't the advice you wanted but just keep this in mind when you're running for this achievement. Even with all these guides it won't make some of these challenges easy, it'll just make them easier. They'll still be tough as hell. Just keep at it, you'll get it eventually.

And on to the good stuff:

ROSWELL: The High Deck Gap is one of the most annoying gaps to get in the whole game, but once you nail it the rest of the follow-up is pretty easy imo. Just hit the L+R triggers when you get close to clearing the deck. If you trigger an Acid Drop it'll magically pull your character the rest of the way into the half-pipe and easily secure the gap for you. The Acid Drop will only trigger if you're getting really close to making the gap though, meaning this'll only help you with those last few inches so make sure you're still getting plenty of speed and air with maxed stats and the wall-plants/Acid drop combo on the opposite side of the pipe shown in the videos. Personally I recommend making sure you hit the High Deck Gap onto the roll-in side of the pipes so you can just grind around the halfpipes, manual up through the observation room and grind down the three rails to easily secure the challenge.

SCHOOL II: WOW, this challenge SUCKED. This one easily took the most time for me to get down. I attempted the route shown in both guides before me but I just couldn't get it down and found a new way that may or may not be easier for you:

Start with the Roll Call Nightmare Rail! with as little speed as possible because once you hit the ground you want to manual and hit a hard u-turn and grind up the sloped path back to the start. You will have to jump and grind once or twice to get enough speed to make it all the way up.
Take the sloped path on the left and turn the corner to hit the Roll Call Opensezmee Rail. Proceed to the Gym Rail 2 Rail and onto the Roll Call Gonz Rail! from there. If I can figure things out, I'll make a video to better illustrate this path.

THE BULLRING: Just follow this video
It is infinitely easier to start with the stupid Launch to Banana since it is ridiculously hard to line it up mid-combo. Once I saw you could just grind the halfpipe rail, wallplant the roll-in, and grind the halfpipe rail again for the Nailin` the Rail gap; it blew my mind. Literally went from an hour+ of trying to 2 attempts to finish this level.

Other than those three levels, I pretty much had the same routes-ish as everyone else except for School 1 where I did their recommended route backwards because I am a masochist. Seriously would not recommend it. If you can get School II done, you can get every other level done. It was easily the most nightmarish of all the routes. Hope this helps!