Comedians Cup Round 2: Part 1 of 8

ROUND TWO, PART 1 of 8 (CHICAGO)

Ah, Chicago! Birthplace of Modern Improv!
It's got Second City! It's got I.O.! It's got the Annoyance!
It's Mecca for every comedy performer who has splashed in the deeper waters of improvisational magic, and it's where the first part of the Round 2 bracket will "take place!"

Fun fact: The Southeastern Comedy Arts Alliance is a brotherhood of improv troupes that span across almost a dozen southeastern U.S. states. It has 16 member troupes. Meanwhile, according to FuzzyCo, there are over 65 improv troupes just in Shytown. Yeah.

73. JOE ROGAN (Stand-up comic, Fear Factor, UFC)
vs.
(#1) WILL FERRELL (Old School, Anchorman, Zoolander)

Kary: Most people are familiar with Rogan from UFC and Fear Factor, but the guy is really smart and interesting (I read his blog). Unfortunately I've never seen his comedy work. Will Ferrell, however, I am intimately familiar with his comedy. And when I say "his comedy" I mean HIS COMEDY. Give me Will.
Gabe: Though he never co-starred on "NewsRadio," something in me (call. me. craaazy) gives the edge to that young upstart Ferrell. Mark my words, he's goin' places.
James: Joe Rogan's a funny guy. He does quality stand-up work. And I really have a lot of respect for him after seeing a lot of that Carlos Mencia stuff unfold. That said, he got a tough first round draw. Ferrell.

Kary: WILL FERRELL
Gabe: WILL FERRELL
James: WILL FERRELL

WINNER: *WILL FERRELL*

74. BRIAN POSEHN (The Sarah Silverman Program, Just Shoot Me, Mr. Show)
vs.
RAINN WILSON (The Office, Juno, My Super Ex-Girlfriend)

Kary: Rainn is one of if not the best things about The Office. And who could forget his nutty but caring teacher role in The Last Mimzy? "The eyes are the groin of the head." Rainn.
Gabe: Battle of the nerd comics, geez! Gotta go with Wilson. For Office line deliveries like the one about trouble hiring Jack Bauer as his ideal second-in-command: "He is unavailable, fictional, and overqualified."
James: I like Brian Posehn, but again, tough draw. I have laughed more due to Rainn Wilson's antics, and Posehn's dryness works best as part of an ensemble, in the way he provides wry, subtlety to complement Sarah Silverman's insanity. But alas, my job isn't to judge ensembles. It's a solo competition.

Kary: RAINN WILSON
Gabe: RAINN WILSON
James: RAINN WILSON

WINNER: *RAINN WILSON*

75. OWEN WILSON (Shanghai Noon, Starsky & Hutch, Wedding Crashers)
vs.
(#8) DREW CAREY (U.S. Whose Line, The Drew Carey Show, The Price is Right)

Kary: Owen does what he does well. I really enjoyed the Chan/Wilson pairing in Shanghai Knights. Drew is kinda dorky and goofy and I can appreciate that. He also doesn't discriminate between the hotties and the not-so-hotties on The Price is Right when it comes to letting them hang on him and kiss him. That scores points with my grandpa and so scores points with me. Drew.
Gabe: Less funny than he was a year ago, for sad reasons, and that funny quotient may diminish even more after Drillbit Taylor, but I'll give Owen Wilson my vote, for my fond memories of Shanghai Noon and especially for his Wes Anderson projects. "Everyone knows Custer died at the Little Big Horn. What this book presupposes is... maybe he DIDN'T?"
James: Owen Wilson does nearly the same thing every time. So does Drew Carey, but it usually is just annoying to me. Drew Carey has more quality in the stand-up comic type flavor of comedy, so his writing has to get factored into his performance. But Owen doesn't write his own material, right? I'm gonna say wrong. Wilson co-wrote The Royal Tenenbaums, so even the stuff Eli Cash did in it I'll have to consider "Owen Wilson's own material"... so... yeah, I'm gonna take Owen Wilson as an upset. He's got a schtick he does, but it's charming and it usually works on me.

Kary: DREW CAREY
Gabe: OWEN WILSON
James: OWEN WILSON

WINNER, AND NEW #8: *OWEN WILSON*

76. MOS DEF (Hitchhiker's Guide, Be Kind, Rewind, The Italian Job)
vs.
A. WHITNEY BROWN (The Daily Show, SNL)
Kary: "I said I had a bad experience." Mos Def.
Gabe: Mos Def, mos' def'. HAHAHHAHAAAHAHA (*cue canned laughter*) Oh, oooh, whoo.... sorry... woo... man, sometimes, I just.... whoooooooo.
James: Of the two of them, Mos Def is the ONLY ONE WHO'S EVEN BEEN DOING COMEDY IN THE 2000's. Hello?! Remember, I'm the one who didn't know why A. Whitney Brown even made it to Round 2 to begin with. Besides that, Mos Def is funnier, too. Most definitely Mos Def.

Kary: MOS DEF
Gabe: MOS DEF
James: MOS DEF

WINNER: *MOS DEF*

77. LEWIS BLACK (The Daily Show, Stand-up comic, Accepted)
vs.
(#4) EDDIE MURPHY (Shrek movies, Norbit, Daddy Day Care)

Kary: I've always been an Eddie fan. I can't say he's been huge in the 2000s but he's great in Shrek. Lewis Black is a revered comic but I don't know much of his work. Eddie.
Gabe: Oh, ouch. Tough, tough match-up, in my mind at least. Eddie Murphy, horrible film choices aside, is a legend. Black is one of my favorites of the moment, the curmudgeon comic writ large, frothing with endless venom for any number of worthy targets political and otherwise. But, as has been the slant of the proceedings, I'm supposed to spend more time considering performance than writing, and in that light, I'm gonna have to appease my gut and say Eddie Murphy. Was he funnier back in '85? Yes. And no. When the material he works with is good (I know, I know, it never is), he can still hammer it home with energy and bite that remains, over 20 years later, as good as it once was. Don't look to turds like Norbit for evidence of this. Salvage what little you can from his Shrek voiceovers and his incendiary supporting turn in Dreamgirls. And, I'm sure, all of this leaky justification for Murphy will have been in vain, as I smell a Lewis Black steamroller chuggin' 'round the bend, righteous indignation at the wheel. But... Eddie freakin' Murphy!
James: Wow. Now this is what the Comedians Cup is for. I just didn't expect such an epic clash so early. Eddie Murphy will always be legendary for the early half of his career. His SNL stuff, 48 Hours, Coming to America stuff. He truly is a legend. But this is the 2000's, and all the Norbit, Nutty Professor, and Haunted Mansion in the world can't beat one good Lewis Black rant on the state of American politics.

Kary: EDDIE MURPHY
Gabe: EDDIE MURPHY
James: LEWIS BLACK

WINNER: *EDDIE MURPHY*

78. AMY POEHLER (Upright Citizens Brigade founder, SNL, Blades of Glory)
vs.
CEDRIC THE ENTERTAINER (The Original Kings of Comedy, Stand-up comic, Barbershop)

Kary: Cedric is funny, no doubt. But I want to squeeze Amy Poehler because she's so cute and funny. Amy. Plus Will Cooper has seen her live....so (hah stole your thunder in the comments, Will).
Gabe: Cedric. Yep. Barbershop and Intolerable Cruelty were both in the 2000s, and his performances in both made me laugh more than the combined library of Poehler material. There, I said it.
James: I like both of these performers, but I'm gonna go with Ced.

Kary: AMY POEHLER
Gabe: CEDRIC THE ENTERTAINER
James: CEDRIC THE ENTERTAINER

WINNER: *CEDRIC THE ENTERTAINER*

79. CARROT TOP (Stand-up's "prop comedy" man)
vs.
(#5) JACK BLACK (School of Rock, Nacho Libre, Orange County)

Kary: I'm afraid of JB becoming nothing but a caricature in any role he plays but I love him all the same. Jables.
Gabe: Oh, Carrot Top, we hardly knew ye... Jack Black.
James: Oh, woe is me, Carrot Top! I really wanted to see Carrot Top go to Round 3. But in this match-up, it just can't happen this time.

Kary: JACK BLACK
Gabe: JACK BLACK
James: JACK BLACK

WINNER: *JACK BLACK*

80. RACHEL DRATCH (SNL, 30 Rock, various)
vs.
JOHN MICHAEL HIGGINS (Christopher Guest movies, Walk Hard, Arrested Development)

Kary: Of course I have a soft spot for former SNLer Rachel, I think she's great. JMH brings something special to the roles he plays and I always enjoy watching him. JMH.
Gabe: John Michael Higgins, for the same reasons I listed in the first round.
James: Both of these comedians are great. And I almost picked Dratch, because of some of her riotous contributions to SNL. But I think Higgins might have a bit more range, so I think to me Higgins edges her out by just that much.

Kary: JOHN MICHAEL HIGGINS
Gabe: JOHN MICHAEL HIGGINS
James: JOHN MICHAEL HIGGINS

WINNER: *JOHN MICHAEL HIGGINS*