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