Credit: Pacific Coast News Photo: A Dapper Scott Disick Hails a Cab in New York City on November 6, 2010

Scott Disick is one messed up dude, and thanks to Keeping Up with the Kardashians and Kourtney & Khloé Take Miami, his most cringe-worthy moments have all been captured on camera... and broadcast to the nation. Although he's now sober and doing his darndest to be a stand-up father to little Mason and boyfriend to Kourtney Kardashian, it's possible he'll slip up at least once on this season of KUWTK. We've assembled five of his most memorable gaffs and meltdowns for your viewing pleasure. We can only hope he outdoes himself in the latest Kardashian spin-off!

5. Bruce knows best (Season 4, Keeping Up with the Kardashians)
Over lunch, Bruce Jenner gives it straight to Scott about his less-than-admirable behavior.

4. Catching up with Scott is downright scary...
Relive many groan-inducing Scott moments — including his Vegas scene with the waiter — in this priceless recap clip.

3. Party monster (Season 4, Keeping Up with the Kardashians)
When Scott and the boys go out and tie one — or many — on, they return to the Jenners' house at 3 AM only to find Bruce awake… and in a rage.

2. Scott gets sloppy (Season 4, Keeping Up with the Kardashians)
Rob and Scott go drinking. While getting extremely inebriated, they discuss the reasons Kris Jenner disapproves of Kourtney's boyfriend.

1. Scott hits rock bottom (and breaks a mirror) (Season 2, Kourtney & Khloé Take Miami)
Kourtney confronts Scott about his partying, and Scott absolutely freaks out and breaks a mirror while Mason is in the other room.