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The 25 Funniest Web Videos (No, Really!)

From "Star Wars Kid" to Bill O'Reilly's meltdown, a gallery of YouTube's greatest hits. By Aaron Burgess

Aaron Burgess

Posted Sep 18, 2008 9:01 AM

Fat Kid on Rollercoaster

Poached from Australia's Funniest Home Videos, this viral classic finds a rotund kid losing his shit — and nearly his seat — on a coaster while the woman next to him obliviously yuks it up.

Highlight: 0:16-:24 — from thrilling to scary to hilarious in seconds.

McDonald's Rap

In 2006, two amateur MCs from Indiana beatboxed their order into a Mickey D's drive-thru speaker, inadvertently launching a thousand lame viral-marketing campaigns in the process.

Hightlight: 0:42 — a cashier asks, "Can you throw that down again?" and inspires the boys to chop, screw and speed up their order in real time.

Toilet Prank

Visitors to a port-a-potty fall prey to one of the better pranks on YouTube when their john door magically transforms into the entryway of a corporate boardroom.

Highlight: The polite older gentleman who, at 0:47, apologizes before retreating back into the crapper.

Cop Eats Pot Brownies and Freaks Out!!!

On this May 2007 MSNBC clip, a Michigan cop unwisely calls 911 after eating brownies made from stolen evidence. The dispatcher asks what we're all thinking: "Do you guys do this on a regular basis?"

Highlight: "I think we're dead, I really do. Time is going by really, really, really slow." Dude, in some circles, that's called peaking.

Zombie Kid Likes Turtles

Cornered for a live on-air chat about how he's enjoying the day's festival, a face-painted grade-schooler renders his interviewer hapless with the retarded equivalent of a Zen riddle: "I like turtles!"

Highlight: That pause at 0:10 — you can practically hear the tires screeching.

Crazy Frog Bros

German production crew Bass Bumpers once knocked Coldplay down the U.K. charts with their version of the '80s synth hit "Axel F" — a.k.a. the "Crazy Frog Song." In this 2006 clip, however, it took just two lip-syncing dorks in a basement to crush them all.

Highlight: 2:08 — where the hell did that rope swing come from?

Whistle Tips with Bubb Rubb

Oakland, California, whistle-tip aficionados Bubb Rubb and Lil' Sis became Internet celebrities after this 2003 TV-news segment on the annoyingly high-pitched muffler mods hit YouTube. All together now, y'all: "Whoo-whoo!"

Highlight: 1:53 — Bubb Rubb nearly crashes his car while showing off his tips on the open road.

Dramatic Lemur

This literally eye-popping primate footage would find itself paired up with all sorts of ridiculous soundtracks, but for sheer dramatic effect (and big, dumb laughs), nothing beats hearing it with the THX theme. Dramatic Chipmunk, consider yourself pwned.

Highlight: Wait... for... it.

Grape Stomping Lady Falls!

Fox 5 Atlanta reporter Melissa Sander takes a massive, gruesomely audible faceplant while stomping grapes during a live segment. One of Howard Stern's most memorable sound effects is born.

Highlight: 0:55-:57 is the reason YouTube's pause button exists.

What Really Happened to the Life Size X-Wing

This 2007 clip is even funnier if you know the back story, in which a crew of California geeks spent months readying their own life-sized, rocket-powered X-Wing Fighter for launch. At least until the Empire gets wind of their plans...

Highlight: 0:12-:13 — a Lucasfilm résumé in YouTube form.

Bill O'Reilly Flips Out — Dance Remix

O'Reilly's Inside Edition-era meltdown over a malfunctioning TelePrompTer had barely gotten cold on YouTube when this dance remix surfaced in May of 2008. It's since graduated to the iTunes store.

Highlight: The whole thing is priceless — as creator levmyshkin says, "Everyone who turns this song into a ringtone is my hero."

Sesame Street Casino — Elmo and De Niro

The synchronization may be a little wonky, but just imagine a 5-year-old stumbling across this mashup of Elmo (as Joe Pesci), De Niro and a particularly NSFW scene from Casino — you mudderfucker, you.

Highlight: 0:6-:11 — Pesci's F-bomb syncs perfectly with Elmo's mouth.

Grindcore Wedding

In this 2006 mashup, the squarest-looking wedding dance in history gets a welcome shot of heavy-metal adrenaline, while low-rent grindcore band Cock and Ball Torture actually gets over a million people to pay attention to one of its tunes.

Highlight: The way the riff syncs up with those dancers at 0:19 is just uncanny.

Benny Lava

YouTube user buffalax specializes in rendering non-English music videos absurd via subtitles. In this 2007 clip, buffalax also manages to catapult Indian choreographer/actor/director Prabhu Deva (rechristened "Benny Lava," after a misheard lyric) into global Internet-meme status.

Highlight: 3:35-3:40 — "I fought a barber man / We know what's in butter rum." Us, too!

Scary "Mary Poppins" Recut Trailer

In 2006, Georgia film student Chris Rule recut the Disney classic into a trailer whose sheer terror rivals The Exorcist. But is it funny? That depends — when was the last time you watched Mary Poppins without wishing bad things on Julie Andrews?

Highlight: Mary's joyful head-spin horribly recontextualized at 0:41.

Guinea Pigs "Highway Star" Video

In a rare moment of cuteness, the acid-fried Clevelanders behind the underground party-tape series The Crazy Dave Tape pull their editing bay away from porn and gore long enough to sync Deep Purple's "Highway Star" to some idiotic footage of driving rodents.

Highlight: The last five seconds — wha?

Barack Roll

A meme poking fun at a meme. Aussie lawyer and Internet jokester Hugh Atkin's August 2008 parody of the bait-and-switch clip Rickroll is just as notable for the sheer amount of campaign speeches (not to mention all that Ellen footage) Atkin had to wade through to splice it together.

Highlight: 0:20-1:00 — those are some quick changes we can believe in.

Bar Mitzvah That's What Friends Are For

This monsterpiece of found footage from a 1993 bar mitzvah casts newly crowned man "Seth's" family in a karaoke disaster filled with so many amazing audio and video non-sequiturs (pay attention to that blue screen), you'll swear you were watching a 1960s surrealist happening.

Highlight: Watch the heads start floating at 1:08.

Flea Market Montgomery Commercial

Alabama flea-market proprietor Sammy Stephens found his empire of one thrust into Internet stardom after this low-budget, so-bad-it's-genius rap hit YouTube in 2007. Once Ellen got hold of it, the whole world would follow.

Highlight: 0:11-:12 — Andre and Big Boi got nothin' on Stephens' delivery of his immortal tag line: "It's just like a mini-mall!"

Kid Impersonates Napoleon Dynamite During Spelling Bee

Dominic Ranz Ebarle Errazo may not have won the 2005 Scripps National Spelling Bee, but after his completely out-of-context Napoleon Dynamite reference hit YouTube, the kid became an overnight sensation.

Highlight: 0:33, when the announcer asks the TV audience, "Was that a secret message?"

Porn Call to QVC

Calling in live on-air to QVC for the company's 18th anniversary, proud Dell computer owner "Randy" (fitting name, that) makes no bones about all the boners that new system has him popping.

Highlight: 0:47 — Randy manages to squeeze in one more "porno" before hanging up.

Dildo on the News

Covering a major cocaine bust in Maplewood, Minnesota, a Channel 5 Eyewitness News reporter prefigures Andy Samberg's viral work with this rather impressive, if accidental, "Dick in a Box." Pay attention to that door.

Highlight: 0:19 — he seriously has no idea.

Boom Goes the Dynamite

In this 2007 clip, Ball State freshman Brian Collins proves he's no great improviser, but after accidentally spawning an Internet meme while calling a play-by-play out of sheer frustration, the dude would still go on to David Letterman and a full-time TV gig.

Highlight: 2:30 — a catch phrase is born.

Top 10 Angry On-Camera Meltdowns

YouTube is a veritable treasure trove of short-circuiting TV-news-anchor footage, but from Chris Berman's freakout to Sue Simmons' F-bomb, this 2008 clip gathers the best of the worst in a (well-coifed) hair under two minutes.

Highlight: 0:25-:43 — the on-air pissing match between WYNY-TV's Jim Ryan and Dick Oliver.

Star Wars Kid

In 2002, a 14-year-old dork films himself on school equipment doing his best/worst Darth Maul, only to have sinister schoolmates lift the footage and make Internet history at his expense. Even as the Web's most popular video (nearly 1 billion views and counting), it's still painful to watch.

Highlight: That painful close-up at 0:43 — he really means it.

Natalie Zfat contributed to this story.