Good Bad Bugs: THUG2 has a brilliant one in the Los Angeles level in Classic Mode. The level was a remake of the one from Tony Hawk's Pro Skater 3 and is built around the same code, being virtually identical. Because of the additions since its original release - getting off your board and skitching) it is possible to jump onto an area of highway you were originally not supposed to go to. There, you can skitch on one of the cars and this will enable you to enter the background, underneath the level. The ground around is solid and you can walk around for quite a while.
Sequelitis: The second game to those who weren't overly thrilled to see THUG's surprisingly good story followed up with "Jackass: The Game". Not to mention the new gimmicks though sometimes pretty fun, largely over-complicated the formula.
Take That, Scrappy!: After inducing much rage in the audience of the first game, Eric Sparrow spends THUG2 screaming like a little bitch and pissing (and shitting) himself. By the time he's eliminated from the tour, even Bam is trying to get rid of him and he's on Bam's team.
That One Level: Chapter 8 in the first game on Sick. The Wallplant Combo Goal is basically impossible in your current state, leaving you needing to do the other four. Party Boat Skate Tricks is fine, but Beat Andrew's Best Combos is a hassle because you need to do all three combos without missing a beat (and, annoyingly, there's a gap right in front of you in the first one that might cause an immediate failure), Bowl Grind is a hassle even after you realize your combo must solely consist of grinds and the path to take, while Prove Yourself tells you to do not one, but two 720 spins, which is impossible until you realize that you can run out of the building you start in, climb onto the roof of the other one, and spine transfer off the ramp at the edge so you stay in the air long enough to get the spin done. Don't forget to Revert. And then you have to climb the building AGAIN and repeat it, this time breaking into a manual when you hit the ground after your revert. Hope you didn't waste too much time.
Past that, the Kill Wallows mission of Chapter 15 is also a pain because of how much of a drag it is to actually hit all the spots it wants you to. Chapter 22, however, is where the game decides it hates you again, giving you the Hangover Cure goal that you can't pass by because suddenly you have to do all three Goals. An NPC called Kalo basically tells you to collect a bunch of useless stuff. Wouldn't be so bad if it didn't involve going through a disgustingly long chain of grinds that has to be executed with as few errors as possible, or you won't have the time to get through it, period. Anonymous Caller and Party Favors are thankfully a breeze, only requiring you to visit a cluster of Non Player Characters and do 20 360 Spine Drops over a radio for Anonymous Caller, and use a car to find a bunch of NPCs respectively. The final Goal, Straight Outta Moscow, is stupid, making you navigate instant failure spots and giving you a night vision filter for basically no reason, but overall not as much of a complete pain as Hangover Cure.