1. When he made everyone laugh and wince at the same time.
ABC Family
2. When he made the perfect self-deprecating joke.
ABC Family
3. When he made a pun so good it took you a second to get it.
ABC Family
4. When he got a little dark.
ABC Family / Via starlitskyandyouandme.tumblr.com
Advertisement
5. And totally inappropriate.
ABC Family
6. When he stayed confident.
ABC Family
7. When he made a clever joke and burned the Browns at the same time.
ABC Family
8. When he really did have the worst catchphrase.
ABC Family
Advertisement
9. When he revealed a superhero's inner life.
ABC Family
10. When he dropped the most devastating pun.
ABC Family
11. When he made a joke that was old-school but effective.
ABC Family
12. When he was a model prisoner.
ABC Family
Advertisement
13. When he realized he doesn't look like Rachel.
ABC Family
14. When he gave us a look into his sex life.
CW
15. When he made an excellent poop joke.
CW
16. When he actually came up with a pretty good rap pun.
ABC Family
Advertisement
17. When his pun was so inappropriate that he couldn't keep it together.
ABC Family
18. When he was the creepiest video date ever.
ABC Family
19. When he was tired of always playing the lady.
ABC Family
20. When he totally burned the then–sitting president.
ABC Family
Advertisement
21. When he came up with a very sexy Boy Scouts pun.
ABC Family
22. When he really did think of the most unusual things.
ABC Family
23. When he thought up the next Hamilton.
ABC Family
24. When he and Ryan could barely hold it together during this game.
ABC Family
Advertisement
25. When he didn't make sense but it didn't matter.
ABC Family
26. When he made this face at an audience member's bald joke.
ABC Family
27. And when he finally fought back.
ABC Family
