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Top 10 Funny Music Videos of the 2000s: The Song Parodies

Posted by Shelley White

Ever since 'Weird Al' Yankovic instructed the public to 'Eat It,' music videos have been ripe for mockery. And rightly so: The line between hip and hilarious is a fine one, indeed. For comedians, the rabid pursuit of cool on constant display in music videos is easy pickings. And maybe it's because comics secretly want to be pop stars, but some of the funniest material of the the past decade has been song spoofs. Here are the top 10 funny music video parodies of the 2000s.

10. 'Like a Boss,' the Lonely Island

In this 'Saturday Night Live' digital short, Andy Samberg is asked in a job performance review by Seth Rogen what he does in the office all day. Samberg recounts a day in the life of "The Bawss," from the mundane to the profane. What begins as a sly send-up of rappers' tendency to proclaim their position at the top of the food chain warps into sordid romantic humiliations and unnatural relations with a giant drug-induced fish. (NSFW)

9. 'Laundry Day (My Freeze Ray),' Dr. Horrible

Neil Patrick Harris plays a lovesick would-be supervillain in this droll number from Joss Whedon's awesome Emmy-winning Web series 'Dr. Horrible's Sing-Along Blog.' Pining over his laundromat crush Penny, the Bad Doctor fantasizes about stopping time with his freeze ray to facilitate his attempts to woo her. It's charming, witty -- and more than a little creepy.

8. 'If You Don't Know Me by Now,' David Brent

It's the perfect illustration of what clueless British 'Office' boss David Brent would think is sexy: all-white attire, billowing gauzy curtains and making love to the camera. Ricky Gervais, the master of the cringe-inducing moment, massacres Simply Red in this byproduct of Brent's ill-fated attempt at a music career. Die-hard 'Office' fans will also want to check out the blooper reel (with Gervais repeatedly bursting into peals of laughter) and a clip of Gervais' real-life foray into music, the little-known '80s New Wave group Seona Dancing.

7. 'White and Nerdy,' 'Weird Al' Yankovic

The granddaddy of video parodists takes on Chamillionaire while also poking fun at his own square persona. Yankovic raps about Javascript, Stephen Hawking, action figures and getting freaky with bubble wrap, with a rat-a-tat flow that's actually pretty impressive. The Donny Osmond cameo is a bit precious, but the smartass couplets are vintage Al: "The only question I ever thought was hard/Is do I like Kirk or do I like Picard?"

6. 'Let's Go to the Mall,' Robin Sparkles

In the second season of 'How I Met Your Mother,' Robin Scherbatsky (played by Vancouver native Cobie Smulders) was forced to reveal her past as Robin Sparkles, Canadian teen pop starlet. Robin's video is a spot-on and gut-busting reproduction of the vacuous teen pop of Debbie Gibson, Tiffany and particularly pre-angst Alanis (whose Canada-only hit 'Too Hot' must be seen to be believed). The lyrics are inane ("Come on, Jessica, Come on, Tori/Let's go to the mall/You won't be sorry") and the fashion is horrifying ("Put on your jelly bracelets and your cool graffiti coat"). Plus, there are long-haired weirdo band members and a food court dance sequence!

5. 'Too Many D---s on the Dance Floor,' Flight of the Conchords

Flight of the Conchords have left a legacy of fine pop music parodies in only two seasons on television. From their Barry White send-up 'Business Time' to the Pet Shop Boys-baiting 'Inner City Pressure,' Bret and Jemaine know how to sharply satirize while still producing some damn fine tunes. Michel Gondry directed this mockery of self-consciously cool electronic music videos. The boys wrap their swimsuit area with sparkling disco balls, and is that really Dennis Franz? (NSFW)

4. 'D--- in a Box,' The Lonely Island

Second choice would have been 'Lazy Sunday,' as that was the 'SNL' digital short that first attained viral ubiquity. But 'D--- in a Box' was many people's first inklings that Justin Timberlake is a really funny guy. The manicured beards, extra-dark shades and awful '80s suits are a fantastic visual gag, especially when worn by the music industry's most slobbered-over pop star. But the funny's mostly about this perfect gift idea for the upcoming Christmas season -- and apparently Hanukkah and Kwanzaa, too.

3. 'Male Prima Donna,' Subtle Sexuality

Two denizens of the American 'Office,' Kelly (Mindy Kaling) and Erin (Ellie Kemper) have formed a pop act, and their first music video, 'Male Prima Donna,' is not all that far off from the real thing: catchy song, wind machine, sassy dance moves and Auto-Tune cranked up to 11. The girls mince around the drab office environs in American Apparel metallic leggings, channeling Fergie and Lady Gaga and Gwen Stefani (check out the 'Rich Girl'-inspired sparkly eye patch and parrot), while guest rapper Ryan (B.J. Novak), aka Mr. Understood, gets pimped out in a white tuxedo and top hat.

2. 'Natalie Rap,' Natalie Portman and Andy Samberg

The adorable pixie goes all gangsta in this 'SNL' digital short. It could easily have turned out weak in the hands of another actress, but this Ivy Leaguer fully commits, spitting harder than DMX ("All those kids lookin' up to me can suck my d---"). In her angry young rapper guise, Portman also claims to be a drug fiend who cheated while at Harvard and ends up throwing a chair at cast member Chris Parnell. Somebody get Princess Amidala a record deal, stat!

1. 'I'm F---ing Matt Damon,' Sarah Silverman and 'I'm F---ing Ben Affleck,' Jimmy Kimmel

When Silverman and Kimmel's ill-fated romance was still going strong, she guested on 'Jimmy Kimmel Live' and presented her beau with this hysterical musical missive. Silverman reveals her carnal relationship to Kimmel's ongoing punchline punching bag Matt Damon with her trademark cheerful tone. A month later, Kimmel took revenge by revealing his love affair with Damon's best bud. It all ends up in a recording studio where the likes of Joan Jett, Robin Williams, Perry Farrell, Macy Gray, Christopher "McLovin" Mintz-Plasse and a tone-deaf Cameron Diaz sing a tribute to Kimmel and Affleck's glorious sex life.

Top 10 Funny Songs

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John Lange

Check out mine:
http://youtu.be/ljw87y9CGN8

March 21 2013 at 6:12 PM Report abuse Permalink rate up rate down Reply

andrewrmaher

http://youtu.be/g50o2yr0oAw

January 31 2013 at 9:07 PM Report abuse Permalink rate up rate down Reply

andrewrmaher

http://youtu.be/g50o2yr0oAw

January 31 2013 at 9:00 PM Report abuse Permalink rate up rate down Reply

Dan Houser

http://www.danhouser82.com/vidz/streaming/dans-so-coolio.htm

May 09 2010 at 1:13 PM Report abuse Permalink rate up rate down Reply

Heather Frank

Great list! If you love music lists, check out my weekly Top 5 Music Countdown show here!

http://girllovesmusic.wordpress.com

November 13 2009 at 5:45 PM Report abuse Permalink rate up rate down Reply

Edc

Where is Mother Lover? That was the best and then On a Boat. Silverman sucks!

November 10 2009 at 3:23 PM Report abuse Permalink rate up rate down Reply

Loretta

"D" In A Box is the best ever!!! I Love Justin Timberlake

November 10 2009 at 9:41 AM Report abuse Permalink rate up rate down Reply

Sabrina Herrington

*sigh* and so the list begin...

November 10 2009 at 7:05 AM Report abuse Permalink rate up rate down Reply

rich

most these videos were terrible wtf

November 08 2009 at 10:20 PM Report abuse Permalink rate up rate down Reply

Mary

If You Don't Know Me by Now, Let's Go to the Mall, Too Many D---s on the Dance Floor, Male Prima Donna and Natalie Rap, where Boring ... i didnt like them they where not funny to me..

November 08 2009 at 8:21 PM Report abuse Permalink rate up rate down Reply