The 25 Funniest Comedy Central Shows of All Time

Modern Family's stranglehold on Wednesday night comedy had to come to an end eventually. Since ABC's award-winning sitcom airs at 9 p.m. EST, though, it's not in direct competition with Comedy Central's all-new Wednesday night lineup, starting with the return of Workaholics at 10 p.m. and The League co-star Nick Kroll's new one-man sketch program, Kroll Show (10:30 p.m. EST). Still, the excitement we used to reserve for funny hotties Sofia Vergara and Julie Bowenis slowly, surely diminishing thanks to Comedy Central's prime time lineup.

Tonight will provide the latest reminder that, when it comes to free-wheeling humor, the all-laughs cable channel is second to none. For superb dramas, there's HBO and AMC, and for quirkier, darker genre shows, you've got FX, but the jokes remain on Comedy Central. First launched way back in April 1991, the network has carved its own, reliable niche with frequent stand-up specials, re-runs of beloved cult favorites like Kids in the Hall and juggernauts like Saturday Night Live, and daring, mostly memorable original programming (feel free to keep forgetting David Alan Grier's Chocolate News).

As Workaholics and Kroll Show get set to incite chuckles, we take a look back at their shared channel's legacy of laughter. Here are The 25 Funniest Comedy Central Shows of All Time.

Written by Matt Barone (@MBarone)

Air dates: August 14, 2012-present
Star: Jeff Ross

When comedian and roast regular Jeff Ross' hilarious Comedy Central talk show The Burn with Jeff Ross received a second season renewal recently, we were quite happy, though also a bit surprised. That lack of certainty comes from the show's minimal media coverage during its recent six-episode run (which kicked off in mid-August).

Those who stumbled across The Burn should be in agreement that Ross' reckless skewering of pop culture happenings and free-wheeling discussions with fellow provocative comedians like Jim Norton, Natasha Leggero, and Marc Maron made the show one of 2012's funniest surprises.

Air dates: February 11, 2009-April 15, 2010
Star: Demetri Martin

Important Things with Demetri Martin gave highbrow brainiacs a variety show they could call their own. Unlike other Comedy Central sketch programs like Nick Swardson's Pretend Time, Martin's series (executive produced by Jon Stewart) approached humor with a clinical, outside-the-box sensibility.

Each episode revolved around one central topic (i.e., "Power," "Money," "Nature") and featured the former The Daily Show correspondent playing the role of a Socrates-like philosopher and hosting faux infomercials, amongst other tactical bits, en route to producing mirth. Surprisingly, despite its headier conceit, Important Things with Demetri Martin lasted two full seasons. So did Nick Swardson's Pretend Time, however, so maybe we should be mad at Comedy Central here.

Air dates: 1997-1998
Stars: Ken Ober, Mark Cohen

On Make Me Laugh, comics told all of their original jokes before a stone-faced, serious contestant hoping to earn a dollar for every second that he or she didn't laugh. Is there any better test for a comedian to see if they're actually funny?

We think not, and Comedy Central's resurrection of the aged property (it premiered on ABC in 1958 and thrived in syndication from 1979 through 1980) gave stand-up pros like Kevin Meaney, Doug Stanhope, and The Amazing Johnathan room to test out material while routinely trying to save face in the presence of steely, unflappable competitors.

Props should individually be awarded to the late Ken Ober (pictured above), Make Me Laugh's first-class host, who'll forever be lauded for his work on the awesome MTV game show Remote Control.

Air dates: June 4, 2009-present

Whether you think he's hilarious or obnoxious, there's one thing about Daniel Tosh that's undeniable: The man really is a pioneer. Debuting way back in June 2009, the former stand-up comedian's web-centric show Tosh.0 brought the Internet phenomenon of skewering viral videos and embarrassing YouTube clips into the world of primetime television.

The same week that Tosh.0 premiered, so did the similar Web Soup, but it's clear which property earned the most popularity. in the three years since. In better ways that Web Soup, Tosh's small-screen baby took the format of classic, like-minded programs like Talk Soup, modernized them for the cyber age, and, as a result, inspired subsequent copycats like MTV's Ridiculousness. And as the Tosh-produced Comedy Central cartoon Brickleberry suggests, he's not about to stop calling shots anytime soon.

Air dates: March 17, 2010-present
Stars: Matt Oberg, Kurt Metzger, Natasha Leggero, Randy Pearlstein, Michael-Leon Wooley, Larry Murphy

Props go out to Comedy Central’s brass for sticking with one of its lowest-rated shows, Ugly Americans. Apparently, the network’s big-wigs recognize an underrated comedy gem when they see one, and that’s exactly what they have in this horror fan’s dream come true that, unfortunately, not enough genre die-hards know about.

Ugly Americans is set in a society where famous monsters—i.e., zombies, demons, werewolves, and pretty much every other kind of creature imaginable—go about their normal lives as everyday citizens, and a well-meaning human gets to have hellishly kinky sex with the busty, ever-horny daughter of a Hades native. Yes, our actual reality sucks in comparison.

Air dates: July 28, 1997-January 31, 2003
Stars: Ben Stein, Jimmy Kimmel, Nancy Pimental, Sal Iacono

Pop culture enthusiasts knew Ben Stein from his droll, lifeless, though funny scenes in the 1986 flick Ferris Bueller's Day Off ("Buellller? Buellller?"), but one look at his résumé shows that he's much more professionally decorated than that. As in, he was both a speechwriter and lawyer for presidents Richard Nixon and Gerald Ford. Clearly, he's a brainy guy.

Hence Comedy Central's unconventional game show Win Ben Stein's Money, in which host Jimmy Kimmel would ask contestants trivia questions to see if they were smart enough to beat the eponymous, and proud, nerd. In reality, though, Stein never actually feared that he'd lose his own cash, since the winnings were pooled together from a prize budget, not his savings account. See, we told you he's shrewd.

Air dates: March 12, 2008-October 1, 2008

Considering that abrasive, explosive comedian Lewis Black seems to hate pretty much everything in existence, the premise behind Lewis Black's Root of All Evilis quite clever. Rather than have Black simply spew out indictments toward random pop culture issues, co-creators Scott Carter and David Sacks whipped together a cleverer set-up: Black would moderate a faux "courtroom" where two comics would debate the merits of two opposing topics, before, ultimately, one subject was anointed as "the root of all evil."

Performed with a deadpan self-awareness by all involved, Lewis Black's Root of All Evil allowed its participants to crack jokes while also demonstrating their societal alertness. Thus, you got Patton Oswalt analyzing the importance of YouTube, Greg Giraldo finding ways to promote Paris Hilton, and Andrew Daly vouching for boob jobs. OK, so it wasn't exactly Real Time with Bill Maher, but, nonetheless, it worked.

Air dates: October 17, 2004-November 14, 2007
Stars: Adam Carolla, Jess Harnell, Abbey DiGregorio, Jack Plotnick, Tara Strong, Cree Summer, James Arnold Taylor

What an exceptional idea: Poke fun at the crowded reality TV market by tossing a ragtag group of animated stock characters into a house and cranking the parental rating up to somewhere in between PG-13 and hard-R.

A wacky cult hit that united a chauvinistic Superman knockoff with a murderous Pokémon ripoff, a boozing Betty Boop lookalike, and other familiar oddities, Drawn Together pushed the boundaries of good taste by making once-kid-friendly cartoons indulge in all of reality television’s sordid indulgences. Just watch Princess Clara and Foxxy Love kiss and tell us it’s not pretty hot. If you’re into that sort of thing, of course.

Air dates: May 28, 1995-December 24, 1999
Stars: Jonathan Katz, Jon Benjamin, Laura Silverman, Will LeBow, Julianne Shapiro

Consider Jonathan Katz a victim of bad timing. Had his dryly funny animated series Dr. Katz, Professional Therapist existed on Comedy Central during its apex of popularity (read: the last decade), it'd most likely receive higher levels of acclaim than it currently does, which is, of course, a shame. In many ways, it's the forbearer to 'tons like South Park, Drawn Together, and Ugly Americans, proving that Comedy Central could produce animation that's adult, edgy, and smartly comedic.

A working comedian before the show's May 1995 premiere, Katz parlayed his unique brands of sarcasm and neuroses into a series that welcomed other popular comics onto its titular character's psychotherapy offices. Amongst the funnymen, and women, who entertainingly had their brains examined on Katz couch were Ray Romano, Joy Behar, Louis C.K., Janeane Garofalo, Jon Stewart, and Rodney Dangerfield.

Air dates:June 17, 2003-August 5, 2003
Stars: Gary Busey, Adam de la Peña

Whoever originally conceived the regrettably short-lived I'm with Busey deserves a lucrative development deal at Comedy Central, immediately.

It's a genius premise: An anonymous, hungry writer (Adam de la Peña) meets Gary Busey, one of his all-time favorite Hollywood actors, starts hanging out with him, and quickly realizes that Busey is certifiably batshit crazy. And wackiness ensues.

The craziness ran rampant, from Busey dressing up as a woman to teach his new buddy that "all men are failed women at birth," to the eccentric star grilling a dead badger and violating an airport bystander's personal space in order to see if he's an bioengineered alien. Even if its reality TV conceit was on the same bullshit level as, say, Jersey Shore, I'm with Busey admirably took creative risks on its way to a strange but singular legacy.

Air dates: July 7, 2006-August 9, 2006
Stars: Matt Walsh, Zach Galifianakis, A.D. Miles, Andrea Savage

When The Hangover premiered in June 2009 and broke box office records, casual viewers wondered where the hell this Zach Galifianakis dude came from—how could a comedic actor as uniquely bizarre as the guy who played Wolfpack organizer Alan come out of nowhere so quickly? Well, he didn't. Long before The Hangover, Galifianakis was working the stand-up circuit like any other struggling humorist, and in 2006, he scored what could've been his initial breakthrough role.

Unfortunately, Comedy Central's Dog Bites Man only lasted one season, but those nine episodes sure made us laugh. Along with his equally proficient co-stars Matt Walsh (currently seen on HBO's Veep, A.D. Miles (the head writer on Late Night with Jimmy Fallon), and Andrea Savage (a Groundlings veteran who's since appeared on shows like Party Down and Two and a Half Men), Galifianakis satirized local news stations by covering low-level happenings around Spokane, Washington.

Dog Bites Man was at its best, though, whenever the foursome fooled real people into thinking they were a legitimate news team—think the funniest man-on-the-street moments from The Tom Green Show, but much funnier.

Air dates: June 23, 2002-2005
Stars: Tony Barbieri, Adam Carolla, Jimmy Kimmel, Tracy Morgan, Kevin Nealon, Biz Markie, Wanda Sykes, Sarah Silverman

Does anyone even make prank phone calls anymore? It seems like a practice that went the way of MTV's The Grind, slap bracelets, and every other long-gone hallmark of our childhoods. Perhaps revisiting Comedy Central's unique Crank Yankers (2002-2007) could bring forth the revival of fake names like "Seymour Butts" and "Ben Dover" and jokes about running refrigerators.

Created by Jimmy Kimmel, Adam Carolla, and Daniel Kellison, Crank Yankers provided comedians like Sarah Silverman, Tracy Morgan, Fred Armisen, and Dane Cook the opportunities to piss off unseen targets, or "marks," over the telephone, while the fake scenarios were played out with puppets. And with characters like elder, crazed Vietnam War vet Dick Birchum (voiced by Adam Carolla), football player turned awful rapper Landalious "The Truth" Truefield (David Alan Grier), and Karl Malone (Kimmel's impersonation of the NBA great), the eccentric humor was always good for some uncomfortable laughs.

Air dates: April 6, 2011-present
Stars: Adam DeVine, Anders Holm, Blake Anderson, Kyle Newacheck

Face the facts: Adam Sandler's movies suck nowadays, Harold & Kumar have lost their mojo, and Seth Rogen is, successfully and to his credit, stretching out his dramatic skills. There's a clear void for shamelessly dumbass-friendly comedy in theaters lately, but on TV screens three corporate American slackers are helping us remember what it's like to laugh at numbskulls.

Obviously smarter than the characters they play, Workaholics stars, and creators, Anders Holm, Blake Anderson, and Adam DeVine are currently keeping the underachiever sect of comedy alive and well on their hilarious Comedy Central series.

For the uninitiated, you can first read our in-depth digital cover story with the fellas. But here's an appropriately simple Workaholics synopsis: It's about three disenchanted employees working for the fictional telemarketing company Telamericorp (Anders, Holm, and Anderson) who'd rather get high and goof off than do any actual work. That's precisely what they do, too, and lovers of mindless laughs are all the better for it.

Air dates: February 1, 2007-April 15, 2010
Stars: Sarah Silverman, Laura Silverman, Brian Posehn, Steve Agee, Jay Johnston, Tig Notaro, Paul F. Tompkins, Mark Cohen

These days, female comedians are all the rage on TV—just look at how far Tina Fey (30 Rock) and Amy Poehler (Parks and Recreation) have come, recently hosting, and killing it at, the Golden Globe Awards broadcast. One hilarious lady who's also worthy of big things is Sarah Silverman, a widely known performer who's yet to reach those Fey/Poehler heights of notoriety. The thing is, though, that Silverman probably likes it that way.

Why? Because her edgy, take-no-prisoners brand of humor isn't built for NBC or basic network television. Given the freedom to push boundaries on The Sarah Silverman Program, the potty-mouthed but clever comedienne subverted sitcom paradigms through sheer inappropriateness.

Take the episode titled "Joan of Arf," for instance, in which Silverman—playing a fictionalized version of herself—gets in trouble for licking her dog's ass in public. Or "A Fairly Attractive Mind," where she tries convincing people that she's mentally retarded. You're not likely to see those plot-lines on Whitney, that's for sure.

Air dates: 1993-1997
Star: Bill Maher

Preceding Comedy Central's The Daily Show by six years, highly opinionated comedian Bill Maher's seminal Politically Incorrect was the first program to bring Washington, D.C., and it's various issues, to the attention of humor-seekers everywhere.

Much like his current HBO program, Real Time with Bill Maher, Politically Incorrect housed the host and four guests (coming from different walks of celebrity, from government to entertainment) discussing, and often heatedly debating, the biggest news stories of the day. And also similar to Real Time, Maher's original series routinely pissed conservatives off, generated controversy, and provided the only platform for people as different as Ann Coulter and Carrot Top to verbally spar over the world's most important issues.

Air dates: June 15, 1999-June 19, 2004
Stars: Jimmy Kimmel, Adam Carolla, Joe Rogan, Doug Stanhope, Bill "The Fox" Foster, Aaron Hamill

Acknowledging the cleverness at work during episodes of Comedy Central's long-defunct The Man Show is, understandably, difficult—you try recognizing satirical wit while the Juggy Dance Squad's scantily clad beauties bounce up and down all up in your face.

Take a second to ignore the jiggling jugs, however, and you'll see that co-creators Adam Carolla and Jimmy Kimmel were responsible for some slick fun-poking aimed at stereotypes of masculinity. Never losing sight of its playful tone, The Man Show exaggerated the things dudes wholeheartedly love (beer, chicks, bikinis, and more beer) in an attempt to salute those vices while simultaneously spoofing those who take them too far.

Air dates: December 9, 2002-November 4, 2004
Star: Colin Quinn

CNN had Crossfire, the debate show that regularly featured lefties like James Carville and Geraldine Ferraro and right-wingers like Tucker Carlson and John Sununu verbally duking it out over worldly issues. Comedy Central, on the other hand, had Tough Crowd with Colin Quinn, and, even though Wolf Blitzer will hate us for saying so, we'll always prefer the latter.

Hosted by veteran stand-upper Quinn, Tough Crowd assembled a revolving panel of his fellow comics on stage to discuss topical issues—and, unavoidably, insult the hell out of each other in the process. The usual suspects included Jim Norton, the late Patrice O'Neal, and Nick DiPaolo, but, every now and then, Quinn welcomed heavyweights like George Carlin and Jerry Seinfeld.

Air dates: August 5, 2001-November 11, 2004
Star: Dave Attell

Dave Attell remains one of comedy's most underrated talents. For recent evidence, catch up with his riotous, raunchy, Mystery Science Theater 3000-esque Showtime series Dave's Old Porn, in which Attell sits down with a notable comedian and an adult film veteran to comment on vintage, low-budget, exceedingly hairy skin flicks. Or simply dig back into the vaults and track down his innovative Comedy Central show, Insomniac with Dave Attell.

Accompanied by a camera crew, Attell proceeded his various stand-up gigs across the country with interactions amongst local bar patrons, passers-by on the streets, and all kinds of other everyday people. The results were unpredictable, unrehearsed, and never underwhelming. It's basically what you and your boys do every Friday night around 3 a.m., except, you know, it's coherent.

Air dates: August 10, 2003-present

Celebrities are adored by millions, sleep on beds covered with dollars of bills, and get to make whoopee with whomever they please—why not enjoy watching them get viciously insulted on national television? That's the magnetic allure of the frequent Comedy Central Roast specials, which the cable network adapted from the New York Friars' Club events it aired between 1998 and 2002.

Over the last decade, Comedy Central Roast victims have included, in no particular order of worthiness, Pamela Anderson, William Shatner, Larry the Cable Guy, Charlie Sheen, and (arguably the funniest broadcast yet) Flavor Flav. Despite the respective presence of a big-name target, the specials' real draws are the small but reliably funny stable of B-list stand-up comics who provide the disses. Our favorites: Jeff Ross, Lisa Lampanelli, and the two late, slept-on Roast greats Greg Giraldo and Patrice O'Neal.

Air dates: July 23, 2003-July 8, 2009
Stars: Thomas Lennon, Robert Ben Garant, Cedric Yarbrough, Niecy Nash, Wendi McLendon-Covey, Kerri Kenney-Silver, Joe Lo Truglio, Carlos Alazraqui, Mary Birdsong, Ian Roberts

Quick to yell “Fuck the police!” whenever a cruiser rolls by and the uniformed driver grills you down? Then Reno 911! is the show for you. The brainchild of The State veterans Thomas Lennon, Robert Ben Garant, and Kerri Kenney-Silver, the Comedy Central mockumentary series tosses pies at police officers with its dumb-ass characters and their knack for busting comically inept criminals, from cross-dressers to dim-witted drug pushers. If cops were this idiotic in real life, the streets truly wouldn’t be safe.

Air dates: 1989-1996
Stars: Joel Hodgson, Michael J. Nelson, Trace Beaulieu, Josh Weinstein, Jim Mallon, Kevin Murphy, Frank Conniff

As our list of the 50 best bad movies implies, we're more than partial to enjoyably crappy cinema around here, which is why Mystery Science Theater 3000 will always hold a special place in our hearts.

Anyone who's ever stayed up late to watch cable airings of shitty old flicks like Robot Monstercan relate to hosts Joel Hodgson (1988-1993), Michael J. Nelson (1993-1996), and their robot pals Tom Servo and Crow. Trapped on an aimlessly traveling spaceship, they're forced to sit through some of the cheapest and most poorly made movies of all time—fortunately, they're endlessly witty and blessed with impeccable comedic timing.

Because of MST3K's resident critics, awful films like Manos, the Hands of Fate, The Crawling Eye, and Viking Women and the Sea Serpent aren't just bearable—they're also wonderful punch line fodder.

Air dates: October 17, 2005-present
Star: Stephen Colbert

The best actor on any original Comedy Central program: Hands down, it's Stephen Colbert. The one-time Daily Show correspondent branched off on his own in October 2005 to spearhead The Colbert Report, an impeccably performed and always spot-on lampooning of righty, blowhard talk show hosts like Bill O'Reilly. Unwaveringly playing a heightened character, a la Sacha Baron Cohen in Borat, Colbert pokes fun at extremist views and conservative ideologies without ever breaking from his role.

OK, the occasional laugh seeps through his demeanor, but who can blame him? With his live studio audience members chuckling uncontrollably at each of his sardonic one-liners and playfully delusional rants, it must be damn near impossible for Colbert not to break out in hysterics with them.

Air dates: January 22, 2003-July 23, 2006
Stars: Dave Chappelle, Charlie Murphy, Donnell Rawlings

Like a potty-mouthed magician, stand-up comedian Dave Chappelle came, quickly conquered, and then disappeared from the public’s collective eye. Whether he truly went bonkers or legitimately questioned his fame is anyone’s guess, and, frankly, it really doesn’t matter, because the genius-level variety landmark Chappelle’s Show holds up as a sharply executed crowd-pleaser that’s leaps and bounds beyond any show of its ilk that’s come in the star’s pop culture exodus.

Air dates: January 1999-present

Remember when Craig Kilborn hosted the first incarnation of The Daily Show. Neither can we. After three years under the marginally humorous Kilborn's watch, Comedy Central's tongue-in-cheek, late night news show underwent a major overhaul in January 1999, when respected comedian Jon Stewart stepped in to takeover hosting duties. And the face of political commentating was forever altered—for the better.

'Tis the age we live in, where most youngsters get their news from two primary sources: Twitter and The Daily Show with Jon Stewart. Which could explain why so many teenagers and twentysomethings are armed with so many sharp, piercing jokes about right-wing dingbats (i.e., Bill O'Reilly, Rush Limbaugh), governmental inadequacies, and an impressive perspective and handle on the world's loftiest issues.

Air dates: August 13, 1997-present
Stars: Trey Parker, Matt Stone, Isaac Hayes, Eliza Schneider, Mona Marshall, April Stewart, Mary Kay Bergman

By now, if you're unaware of Trey Parker's and Matt Stone's animated series South Park, that rock from which you crawled out under might still be there, so you'd best head back thataway. Always peppered with seething indictments against politics, pop culture, and other real-life societal issues, the Comedy Central mainstay's humor—pushed forward by the young foursome of Cartman, Kyle, Stan, and Kenny—has provided the television with some of its smartest comedy for the last 15 years.

It takes a special kind of program to shift from a character that's literally a talking piece of feces (we miss you, Mr. Hanky) to unveiled indictments against everything from George W. Bush to Tom Cruise and The Human Centipede. Thanks to the collaborative genius of Parker and Stone, though (also see their current Broadway record-breaker The Book of Mormon for proof), South Park covers wide terrain with a consistent, always brutally funny intelligence.