The 30 Funniest Political Videos of the Decade

Top Viral Videos of the '00s

The most memorable spoof videos, comedy routines, and political bloopers from 2000-2009.
01
of 30

Stephen Colbert's Bush Roast

In the ballsiest comic stunt ever pulled in Washington, Stephen Colbert delivers a searing roast of President Bush at the 2005 White House Correspondents' Dinner. With Bush sitting ten feet away, Colbert says, "I stand by this man because he stands for things. Not only for things, he stands on things -- things like aircraft carriers and rubble and recently flooded city squares. And that sends a strong message, that no matter what happens to America, she will always rebound with the most powerfully staged photo-ops in the world." (C-SPAN, 2005)

Tina Fey impersonates Sarah Palin in a series of epic "Saturday Night Live" skits, including a joint appearance with Amy Poehler as Hillary Clinton, a parody of Palin's interview with Katie Couric, a spoof of the VP debate, and an appearance with Will Ferrell as Bush. "I can see Russia from my house," Fey's Palin boasts, creating a caricature of Palin that came to define her. (NBC, 2008) More »

03
of 30

Obama Girl Sings 'I Got a Crush on Obama'

Amber Lee Ettinger, AKA "Obama Girl," sings the praises of Barack Obama in this viral hit, which put Obama on the pop culture map. "I cannot wait 'til 2008 / Baby you’re the best candidate / Of the new oval office / You'll get your head of state / I can't leave you alone / 'Cause I've got a crush on Obama." (Barely Political, 2007)
George Bush and John Kerry square off and trade insults in this campaign spoof of "This Land is Your Land," the biggest viral hit of the 2004 presidential campaign. (JibJab, 2004) More »
05
of 30

Letterman Mocks McCain for Bailing on 'Late Show'

David Letterman delivers one of the most punishing beat downs any candidate has ever received on late-night TV. "This doesn't smell right," Letterman says of McCain's decision to suspend his campaign and cancel his appearance on the show. "This is not the way a tested hero behaves. Somebody's putting something in his Metamucil." In many ways, it was the tipping point that sunk McCain's presidential hopes. (CBS, 2008)
06
of 30

Jon Stewart's 'Crossfire' Smackdown

Jon Stewart browbeats Tucker Carlson over journalism ethics during an unforgettable interview on CNN's "Crossfire." Stewart's money quote: "Stop hurting America ... What you do is not honest. What you do is partisan hackery. You have a responsibility to the public discourse, and you fail miserably." The show was canceled shortly thereafter. (CNN, 2004)
07
of 30

Will Ferrell: A Message From the White House West

Comedian and SNL alum Will Ferrell impersonates President Bush trying to film a political ad from his ranch in Crawford, Texas in this brilliant parody. (America Coming Together, 2004)
In this classic SNL skit, Darrell Hammond plays a sanctimonious and sighing Al Gore, who can't stop talking about his "lockbox," and Will Ferrell plays a confused George W. Bush who sums up his candidacy with one word: "strategery." Gore was widely thought to have won the actual debate, but SNL's portrayal of Gore as an over-exuberant and insufferable bore was so devastating that it colored perceptions and helped give Bush the upper hand in the subsequent two debates. (NBC, 2000) More »
09
of 30

Sarah Palin's Turkey Pardon Fiasco

Sarah Palin pardons a turkey while others are slaughtered in the background, completely oblivious to the carnage unfolding behind her. We've learned that when Palin talks, disaster follows, but usually it's not this vivid. (MSNBC, 2008)
In this classic "Daily Show" segment which aired during the Iraq war, Jon Stewart moderates a hilarious debate between President Bush and the one man with the "insight and cajones to stand up to him" -- Texas Gov. George W. Bush. This is Jon Stewart and the Daily Show and its very best. (Comedy Central, 2003) More »
11
of 30

Bush Attacked By Shoes

An Iraqi journalist throws his shoes at President Bush at a news conference in Baghdad, in what becomes known as the "shoe heard 'round the world." The incident sparks a wave of comedy, including amusing Internet mock-ups featuring Bush ducking things like pies and snowballs, as well parodies inspired by Austin Powers and The Matrix. (2008)
12
of 30

Bush Shakin' His Groove Thang

President Bush gets jiggy with it and shows off his dance moves alongside African dancers at a White House event to promote Malaria awareness. Bush dances about as well as he speaks. (2007)

13
of 30

Bill Clinton's 'Final Days' Video

A film crew documents how President Bill Clinton spent his final days in office in this hilarious video, which was originally screened at the 2000 White House Correspondent's Dinner. (C-SPAN, 2000)
14
of 30

Palin Punk'd by Prank Call

A Canadian comedy duo prank calls Sarah Palin and convinces her she's talking to French President Nicolas Sarkozy. Palin fails to pick up on any of the hints that the conversation is a joke, even when he says, "From my 'ouse, I can see Belgium" and praises the documentary about her, Hustler's "Nailin Palin." (Masked Avengers, 2008)
15
of 30

Bush and Blair Sing 'Endless Love'

George W. Bush and Tony Blair express their true feelings for each other as they sing a stirring rendition of "Endless Love." Their war may have gone horribly awry, but their hearts still beat as one. (Kobra, 2003)
16
of 30

Bush's Speechalist

Comedian Andy Dick plays presidential speechwriter Harlan McCraney, the genius behind President Bush's famous flubs. (Comedy Central, 2004)
17
of 30

Sarah Palin Appears on 'Saturday Night Live'

Sarah Palin makes a much-ballyhooed appearance on "Saturday Night Live," where she plays along as Tina Fey skewers her. Palin also participates in a skit featuring Amy Poehler singing a catchy Sarah Palin rap song. (NBC, 2008)
18
of 30

Conan, Colbert and Stewart Unite in Epic Brawl

During the 2007-2008 TV writer's strike, Conan O'Brien, Stephen Colbert, and Jon Stewart resort to fisticuffs to settle a hilarious mock feud over who made Mike Huckabee. (Comedy Central and NBC, 2008)
19
of 30

William Shatner Does Sarah Palin

Sarah Palin's rambling farewell speech baffled many. But Conan O'Brien realized that it was a thing of poetic beauty, and so he invited master thespian William Shatner to read Palin's farewell speech the way it was meant to be heard -- as a beat poem. See also: Shatner reciting Palin's Tweets. (NBC, 2009)
20
of 30

JibJab: Obama the Superhero Has Come to Save the Day!

JibJab presents a brilliant animated video titled "He's Barack Obama," which portrays Obama as a superhero saving the world. It premiered at the Radio and TV Correspondents' Dinner in front of Obama himself, who cracked up as he watched the video. (JibJab, 2009)
21
of 30

Letterman's Top Ten Favorite Bush Moments

At the 2008 White House Correspondents' dinner, David Letterman presents a highlight reel of classic Bush bloopers, including Bush banging his head on the door of Marine One, dropping his dog, and getting foiled by a locked door after trying to escape a reporter's question. (CBS, 2008)
22
of 30

Obama Kills at White House Correspondents' Dinner

In his debut as comedian in chief, President Obama brings down the house at the White House Correspondnets' Dinner with a series of zingers poking fun at himself, members of his administration, and his Republican critics. Obama on the news media: "Most of you covered me. All of you voted for me. Apologies to the Fox table." (C-SPAN, 2009)
Jon Stewart does a brilliant, pitch-perfect imitation of FOX News Channel's resident conspiracy theorist, Glenn Beck, in this classic "Daily Show" segment. There's a war going on in America, and the stakes are nothing less than Glenn Beck's internal organs. (Comedy Central, 2009) More »
24
of 30

John Hodgman Declares Obama A Nerd

Humorist John Hodgman gives a stellar performance as the headliner at the 2009 Radio and TV Correspondents' Dinner. Watch as he teases Obama by calling him the "First Nerd President" and quizzes him on Star Trek, comic book heroes, and other matters pertinent to nerds. (C-SPAN, 2009)
25
of 30

Paris Hilton's Campaign Video

Paris Hilton responds to John McCain's celebrity attack ad with her own campaign video in which she calls him wrinkly and old, and announces her own presidential campaign. (Funny or Die, 2008)
26
of 30

'President' Al Gore Addresses Nation on 'Saturday Night Live'

Al Gore appears on "Saturday Night Live" and addresses the nation from a parallel universe in which he had won the 2000 election. Gore recounts having solved the global warming crisis, providing universal health care, and gives a shout out to Supreme Court Justice Michael Moore and Baseball Commissioner George W. Bush. (NBC, 2007)
27
of 30

SNL Provides Horrifying Glimpse of Palin Presidency

"Saturday Night Live" combines Sarah Palin and the disaster movie "2012" to imagine a world in which Palin wins the presidency. On Election Day 2012, planet Earth is going rogue. (NBC, 2009)
28
of 30

Bill O'Reilly Goes Nuts

Though technically not from this decade, this vintage clip of Bill O'Reilly was unearthed and went viral in 2008. Watch as O'Reilly unleashes an obscenity-laced tirade during his days as host of "Inside Edition."
29
of 30

Wassup 2008

Eight years later, the guys from Budweiser's classic "Wassup" ad return to offer their take on the Bush years and the 2008 election. (60frames, 2008)
30
of 30

Bin Laden Has Nowhere To Run

This animated parody of Harry Belafonte's 'Day-O' (The Banana Boat Song) was viewed by tens of millions of people during the war with Afghanistan. The song, which takes aim at Osama bin Laden and the Taliban, was one of the best parodies that emerged in the post-Sept. 11 period. (MadBlast, 2001)