Funny / Team Fortress Classic

• One of the Medic calls was a disgruntled New Yorker deadpanning "EXCUSE ME, I'm in need of MEDICAL ATTENTION!". It's funny enough on its own due to it coming completely out of left field, but it became even more so when it was revealed in the Team Fortress 2 tie-in comics that Classic Pyro is, in fact, a woman named Beatrice. Who, for reference, still uses the same gruff New Yorker voice as the male characters.
• Many of the game's community maps, most infamously Smear the Queer. The goal of the map is to have someone on one of four teams wear a Teletubby costume so their team can score points over time. The map has a child-like art style; which, combined with the game's overall seriousness, can be quite hilarious to play for the first time.