In the pilot, Gary's boss tells him he'll "have his job" after he cheerfully reveals he made his good trades for only one share each. Gary quits by telling him he can have it and to "keep it in a good place".
When Gary and Chuck argue over the validity of a newspaper that tells the future.
Chuck: Oh yeah! Well I wouldn't let you operate on my coccyx! Now get out!
Poor Chuck's adventures in the hospital, starting with a rectal?
Poor Chuck having a major nervous breakdown in episode 3 of season 1 as he starts seeing pregnant women surrounding him on the streets.
Near the start of episode season 1 episode 4, Gary tries to warn some cooks of the "Wu Ling" restaurant that said restaurant is going to explode, unfortunately, there Chinese and appear not to understand a word of english. A female customer shows up and he tries to get her to translate his warnings. So what does she tell the men behind the counter?
Lady Customer: (in chinese) Is this guy crazy?
Just before that, when he kept saying kaboom. The men behind the counter thought he was talking about the restaurant owner, Gaboom.
Poor Gary getting his hand caught in a door by Meredith.
Gary: My hand. My hand. My hand. My hand. My hand.
While it shouldn't be funny, watching poor Chuck singing a sad song while having to sit out in the rain in order to prevent a mother from leaving her baby on the doorstep of a church in "After Midnight" was pretty funny.
Chuck: (in singsong voice) I'm so cold, I'm so lonely!
The cold open for season 1 episode 8 had Gary stop a fight inside the L train. The three people who start the fight band together to throw him off the train.