The Twenty (Intentionally) Funniest Web Videos of 2007

What works best online? Funny still does. In fact, the Web has become the world’s biggest comedy club, where cutting-edge and too-profane-for-prime-time players—from Hollywood heavies like Will Ferrell to alt-comedy godfathers like Bob Odenkirk—are trying out their best material, for free. Herewith, bookmarks of this year’s twenty best clips of intentional hilarity.

1. R. Kelly’s Trapped in the Closet
R. Kelly’s genre-busting, cliff-hanging, polysexual soap opera signaled the crooner’s ultimate crossover from pop star to radical auteur. Far more experimental than almost anything by guys named Lynch or Van Sant, it was also damn funny. Don’t worry fans: Kelly promises us he’ll keep working on Trapped “till the aliens decide to leave.”

2. Clark and Michael
Beyond Superbad, Michael Cera seemed to pop up in every great show online (Tim and Eric, Derek & Simon). But we most adore Clark and Michael, Cera’s deadpan ten-episode series with his pal Clark Duke.

3. Wainy Days
After years of sketch comedy and the summer-camp sleeper hit Wet Hot American Summer, David Wain has thrown himself into Wainy Days, a Web series that follows his faux dating misadventures in Brooklyn. In one episode, he tries to seduce a dying woman; in another, Rashida Jones plays the female version of Wain, so that he may learn more about being a woman.

4. Dramatic Chipmunk

5. Dave Hill
Dave Hill’s videos on Super Deluxe are mostly Daily Show–style man-on-street reports that rival those of any of that show’s finest correspondents. Hill’s guileless stage presence (and predilection for natty suits) lends an addictive Where’s Waldo? feel to all of his videos—from the New York Comic Con to the Fashion Week tents).
Exclusively for Hill reads a poem, “I Am the Night”

6. Brad Neely’s Washington
A profane, patriotic tribute to our first president (who apparently “ate opponents’ brains and invented cocaine”).

7. Planet Unicorn

8. The Landlord
The Will Ferrell clip that made Funny or Die.

9. All My Exes
In All My Exes, Chelsea Peretti’s six-episode series for Super Deluxe, the lanky New York comedienne dons well-shouldered blazers and conducts interviews, pen in hand, with her fictional ex-boyfriends. Peretti plays the pseudo-journalist with all the soft-focus charm of an early-nineties cable-access-show host.

10. Prank Wars
The phenomenon all started when CollegeHumor editor Streeter Seidell inserted a sex clip into co-worker Amir Blumenfeld’s iTunes—and then filmed his stricken reaction. A war ensued, and public humiliations have since included a fake Jumbotron wedding proposal, and Amir flying to L.A. for a “big break” with MTV. “Amir will tell you he didn’t cry, but he did,” says Seidell. (“Hardly!” says Blumenfeld. “Is it crying when no tears come out? If so, then yes, I might have cried.”)

11. Welcome to My Home Parodies
Former soap star Brenda Dickson’s 1987 vanity video, Welcome to My Home, is a jazzercising, puppy-petting camp classic. Deven Green’s vile voice-over send-ups are parodic masterpieces.

12. Tim and Eric’s Night Live
Relentlessly funny, utterly nonsensical, and poorly miked, these cult heroes (and master prank callers) now stream a live talk show on Superdeluxe.

13. Bob Odenkirk’s Derek & Simon
Comedy’s mad scientist has been using the Web as his laboratory: His series about two lovelorn guys blows up in the most spectacular way. Extra points for the funniest-ever use of a peanut allergy.

14. Alanis Morissette My Humps

15. 300/VOGUE
In a sea of easy parodies, Luminosity’s lush, hilarious pairing of 300 and Madonna’s “Vogue” is the best fan video of the year.

16. St. Sanders
This Finnish rock fan’s Santana Shreds and Eddie Vedder Shreds concert videos look like standard fan tributes, only they’re rescored with outrageously lame guitar solos.

17. Gabe and Max’s Internet Thing

18. Spiders on Drugs
The video of choice among programmers at Film Forum, we’re told, is this drug-addled spoof of nature videos.

19. The Procedure
Willem Dafoe gets his favorite song (“Private Eyes”) surgically implanted in his head.

20. The Jeannie Tate Show
A newcomer with heavy-duty SNL connections, this comedy is hosted in the backseat of a suburban mom’s minivan— and launches six episodes on November 12.

The Twenty (Intentionally) Funniest Web Videos of 2007