WWE 13

Just to clarify, it's 50 destroyed items total.
I never broke any ladders, they're annoying.
Attitude Era counts toward this.
For Tables: leaning tables in the corner of the ring counts, they don't have to be set-up, and announcers tables count.

And you can see how close you are by looking in:
My WWE/Statistics/(Under 3rd tab) Destruction Count

Just as an addition, the announce table counts towards this. As it is cumulative you can knock some out during the Attitude era stories as putting your opponents through the announce table won't result in a DQ.

Just for those who don't want to bash it all out at once.

Use Triple H agianst any wrestler in extreme rules match adjust silders if you wish in you're favour. Then during choose triple h make sure the option for # of finishers is set to infinite so that you can pedigree the oppontent over and over into the tables you can grab from under the ring. So basically grab table pedigree into then rinse and repeat :). Enjoy this easy achievement.

You can also press a while holding table then a agian to put them on top of the table then jump off the nearest corner onto the table to break it. (also easier is the side of ring jumping off will hit and break the table.)

I initially thought that it had to be 50 tables, ladders, and chairs, but it can be just 50 of any of them. Using chairs is the easiest way, have the sliders in the "in-game options" set to your advantage and set up an extreme rules match and go any wrestler and vs any wrestler. It only takes 4 hits to break a chair, plus you'll have some already from Attitude Era mode to go towards it.

Good Luck xP