Skip To Content
  • Viral badge

33 Classic "Whose Line Is It Anyway?" Moments That Will Never Not Be Funny

This post was made with the help of Laura Hall and Linda Taylor!

As a real, human woman, whenever I feel myself getting a little bit blue, I tend to gravitate toward the same classic comforts that I know will, without a doubt, cheer me up...relatable, no?

Walt Disney Pictures

Anyway, one of my personal go-to comfort shows is the first American run of Whose Line Is It Anyway?, which aired from 1998 through 2007!* It brings me back to my childhood, which was spent watching comedy I was way too young for! Thanks mom and dad! (No, really, thank you!)


*I haven't seen the reboot. Not because I don't want to or am anti-reboot...I literally just don't have cable!!! Also relatable!!!!

So, with that in mind, I've taken it upon myself to search the deepest depths of Tumblr to bring you some of the absolute FUNNIEST Whose Line moments from the first American run, compiling them into this easy-to-enjoy list to brighten your day! Sound good? GOOD! Okay, here we go:

1. The time Drew cracked the code on how to get applause:

2. The time Colin said what every president is thinking:

3. And the time Ryan said what every parent is (probably) thinking:

4. The time Wayne was terrified by a shell:

5. The time Colin positively DESTROYED everyone with this deeply weird, random opening:

6. The time Brad out-punned everyone with his dirty mind:

7. The time the boys had this hilarious exchange:

8. The time Colin gave us this horrifying visual:


9. And the time Ryan gave us this equally horrifying visual:

10. The time Wayne brought a joke full circle:

11. The time Ryan gave this confused response:

12. The time Colin shut down Wayne's enthusiastic birth(?):

13. The time Colin gave us an unexpected plot twist:

14. The time Ryan shattered the glass on Drew's desk using nothing but his head:

15. The time Colin didn't hesitate to give us this expert intro:

16. The time Greg and Drew had this fight (and make-up) behind-the-scenes:

17. The time Colin got the hook (in the form of Ryan):

18. And the time Colin delivered this sick burn to Ryan:

19. The time Ryan made things ~inappropriate~:

20. The time Colin shut everyone down:

21. And the time Colin set himself up for maybe the most EPIC pun of ALL TIME:

22. The time Wayne, Drew, and Ryan performed the FUNNIEST "three-headed Broadway star" song in history:

View this video on YouTube

ABC / Via

This is a personal favorite.

23. The time Colin was repulsed by Brad:

24. And, of course, the time Ryan gave us this classic:

WAIT!!! BONUS ROUND!!! Since you've made it all the way through this post and OBVIOUSLY love Whose Line as much as I's a bunch of hilarious screenshots, presented with absolutely zero context, which somehow only stands to make them funnier:


Wayne sitting pretty with text reading "Violently jealous woman who keeps catching people making eyes at her boyfriend, Colin"


Colin making a serious face with text reading, "Gets turned on by danger"


Ryan hunched over with text reading, "Old man who takes and extremely short-acting rejuvenation pill"


Wayne making a wide-eyed face with text reading, "E.T.'s manic frat boy brother who has gone to Earth to party"


Colin at a podium with text reading, "Batman announcing he's coming out of the closet"


Ryan looking suspicious with text reading, "Discovers that his weather map covers the gates of hell and is desperate to keep them shut"


Wayne looking VERY goofy with text reading, "Middle-aged woman proud of her body"


Colin and Chip with text reading, "In the middle of a Broadway Musical"


Ryan looking concerned with text reading, "Fighting the inner urger to be a stripper"

There ya have it! Did you watch the first American run of Whose Line while it aired? Should I watch the new run? What joke/moment/game was your favorite? SHARE EVERYTHING IN THE COMMENTS BELOW!!!