1. Louis CK
What: At the Catch A Rising Star comedy club in his hometown, Boston, CK was in his element; he joked that he knew everyone there. Good thing, seeing as he started off by toying with the audience.
2. Chris Rock
What: Chris Rock was great from a very early age, already unafraid of making blunt, unapologetic commentary on race and politics. Because he was 21 — and still lived at home — he added in a good dose of masturbation humor.
3. Sarah Silverman
What: Commence the self-deprecation, Jewish jokes and border-pushing punchlines tightly coiled in everyday anecdotes. Notice the star-laden audience at The Improv.
4. Dave Chappelle
What: He was the youngest comedian to ever be on Star Search, and already he had a finely-tuned act that blended pop culture, race and frenetic energy. His interaction with Ed McMahon alone had to have caught the attention off the talent scouts.
5. Wanda Sykes
What: First of all, yes, that’s Louie Anderson hosting Comedy Showcase. Now, with that out of the way, enjoy Sykes riffing on timeless topics — New York City’s homeless population — and then more dated subjects, like the JonBenét Ramsey murder case, in ways that still seem fresh.
6. Steve Martin
What: Martin worked as a writer on The Smothers Brothers Comedy Hour, which provided his first big break (and an Emmy). Soon after he joined, he began to land time on camera, already armed with the off-beat jokes and conceptual humor that would ultimately earn him major fame.
7. Seth Rogen
What: “Hello, my name is Seth Rogen and I am a former Playgirl centerfold model,” squeaked the ambitious budding star. The rest is history.
8. Richard Pryor
What: This set, which appeared on the Kraft Music Hall Special, came several years before the re-invention that would turn Pryor into perhaps the most cutting-edge comedian of his time — or any other. Still, you can catch a glimmer of his subversive future, with quick mentions of drugs and a overt mentions of racial tension, which wasn’t easy to do on TV in 1964 — especially for a black man.
9. Simon Pegg
What: An energetic set from the baby-faced Pegg, it was rather English in its particulars but universal in its laughs (the drug talk didn’t hurt).
10. Ellen DeGeneres
What: Her first appearance on The Tonight Show displayed the quick wit, silliness, self-deprecation and charm that allowed her to push the envelope throughout her career. Her haircut is something to cherish.
11. Woody Allen
What: Though he’d been a working writer since 1950, Allen began making TV stand-up appearances in the early 60’s. It was quite fitting that he’d been bumped from Jack Paar’s show several times before getting this slot; being nervous and dismissed would become something he toyed with in his work, no?
12. Larry David
What: Not officially stand-up, but David went on a free association riff during this segment on the SNL-lite show Fridays that just screamed “George Costanza!”
13. Jerry Seinfeld
What: In this, his first appearance on HBO, Seinfeld displayed his trademark observational humor. Also, Richard Smothers looked alarmingly like Ron Burgundy in his funny twist introduction.
14. Mitch Hedberg
What: A few years before he broke out with a hit appearance on Letterman, Hedberg was already delighting and confusing his audience.
15. Janeane Garofalo
What: Two years before she met Ben Stiller and a few more before she joined the staff of The Larry Sanders Show, Garofolo was plying her trade as a big part of the alternative LA comedy scene.
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