Rubber Bandits

You can do this with two controllers or have a friend join your game.

You can pick up items using the B button and you can throw them by holding B and releasing.

I recommend doing this in the starting Jail room and positioning each player in opposite corners of the room then throw an item across the room and hit the other player and the Achievement should unlock.

I show this in my Walkthrough starting at 6:05 minutes into the video.

Can be done with a second controller

Select any game mode and make sure its on "No Teams"

Grab any small item and move your character as far as you can and aim/throw with the button

When you think the item will hit, release the button and the item should hit the other controller, it seems to have a small amount of auto aim, making it easier to hit from a distance.

If it didn't pop, move your character further away if you can

2 controllers - 2 players.
In jail, one on the far left and one on the far right. Grab the baguette with your main player and throw it to hit the other one – if it is far enough the achievement pops.

Check out the video for a fast guide to all achievements:


Timestamps:

00:00 Intro + Successful Escape Achievement M
01:41 Out On Top, Gone in 3 Rounds, Outclassed, Getting Slick, Mastermind Achievements
02:59 Talk about multiplayer + Super Cop Achievement
04:05 Dead Weight Achievement
04:42 Hail Mary Achievement
05:08 Why Thank You
05:33 Inhuman Reactions Achievement
05:54 Clean Sweep Achievement
06:10 Last Man Standing Achievement
06:33 Oceans One Achievement
07:50 Bye Bye Birdie Achievement
08:30 Striking Gold, A Robbers Best Friend Achievement
09:01 Greed is Good, Anger Issues Achievements + Outro

Do this with 2 controllers or with a friend online.
Go far away and throw a small item across at the other player by holding B, aiming and releasing

4:00 Successful Escape
4:35 Striking Gold
5:25 Gone in 3 Rounds
5:25 Outclassed
5:55 Greed is Good
6:20 Anger Issues
7:00 Bye Bye Birdie
8:10 Mastermind
8:35 Oceans One
9:55 Diamond
12:35 Hail Mary
13:10 Why Thank You
13:30 Inhuman Reactions
14:05 Clean Sweep
14:35 Last Man Standing
15:30 Dead Weight
16:15 Super Cop

Achievement Walkthrough: