So ’90s It Hurts: 12 ‘Celebrity Deathmatch’ Videos That Define A Decade

For six seasons, MTV’s Celebrity Deathmatch brought together some of pop culture’s biggest stars to duke it out in claymation form. Now that the show’s first run is more than 15 years old, watching certain episodes is like opening a portal back in time to the 1990s. A warning, though: The ’90s can be a scary place, full of Rachel haircuts and terrible sitcoms. Do you dare journey back with us to the era when boy bands ruled the earth?

James Van Der Beek vs. Saddam Hussein

https://www.youtube.com/watch?v=FkZj9XxjURI

This video highlights two things: how long we’ve been dicking around in Iraq and how long it’s been since James Van Der Beek did anything cool. If you told ’90s me that in 2015, Saddam would be dead and Dawson Leery would be the coolest Power Ranger ever, I’d have said that the future looked bright indeed.

Marilyn Manson vs. Ricky Martin

https://www.youtube.com/watch?v=nWU_h1OtRok

Remember back in the ’90s how newspapers were a thing, and in these newspapers were endless articles about how Marilyn Manson was single-handedly destroying America? How quaint we were back then. That’s the president’s job now. And even though Ricky Martin didn’t come out of the closet until 2010, there’s still enough innuendo in this video to make me think we all knew. Gaydar was another ’90s thing, after all.

The Spice Girls vs. Hanson

In the ’90s, your ability to escape the crap on the radio was limited by your ability to afford $17.99 CDs from HMV and batteries for your Discman. Unless you lived in a shack like the Unabomber, you were gonna hear the garbage bands of the time whether you liked it or not. Which is why everyone from that era knows more lyrics to “Wannabe” than they’d like to admit.

Robert Downey, Jr. vs. Christian Slater

It’s fun to turn the clock back and look at how people treated Robert Downey, Jr. in the ’90s, as a drug-addicted cautionary tale who ruined his career. Who’s laughing now, ’90s? Tony Stark, that’s who.

Lucy Lawless vs. Calista Flockhart

Possibly the most messed up deathmatch of the bunch. For about half the fight, Ally McBeal’s head is literally stuffed up Xena’s butt. Keep your eyes peeled for the dancing baby because ’90s.

Hillary Clinton vs. Monica Lewinsky

You can’t have a “So ’90s It Hurts” list without some mention of the Monica Lewinsky scandal. For a decade, Monica was every lazy comedian’s godsend, and there’s something therapeutic about watching claymation Hillary beating her up. If only she’d gotten a few shots in on Bill, as well.

Jennifer Aniston vs. Courtney Cox vs. Lisa Kudrow

The show that launched a million hair cuts and still haunts the dead zones of bad television channels across the nation. If you’re watching TV and Friends comes on, it’s either 2 a.m. or 2 p.m., and you should be asleep or at work. Either way, your life needs re-evaluating.

Heather Locklear vs. Pamela Anderson Lee

Before Kim and Ray J, there was Pamela Anderson and Tommy Lee. Before Pamela and Tommy, there was Tommy and Heather. So, it makes Celebrity Deathmatch sense to pit the two Crüe groupies against each other. Winner gets to drop Tommy Lee into a pit full of howler monkeys. I hope those monkeys are up to date on their shots.

Melissa Joan Hart vs. Alyssa Milano

What the hell happened to Melissa Joan Hart’s career? One day, she’s winning every Kids’ Choice Award in sight, and the next thing you know, she’s been out of work for a decade and up for something called “The Former Child Star Lifetime Achievement Award.” Perhaps Melissa will fare better in this battle of the cheesy ’90s television witches.

Celine Dion vs. Keith Flint

https://www.youtube.com/watch?v=IakABQVVWr0

This may be hard to imagine, but Celine Dion was even more annoying in the ’90s than she is now. A little movie called Titanic had just come out, and America was experiencing Peak Dion. Meanwhile, every teenager with a Columbia House CD Club subscription was rocking out to Prodigy’s Fat of the Land. It’s a cross-generational battle for the soul of ’90s music.

Fiona Apple vs. John Popper

https://www.youtube.com/watch?v=La7EpaOc00c

To save you some time looking things up on Wikipedia: John Popper is still alive. Yes, Blues Traveler still exists. And Fiona Apple is still as Fiona Apple as ever. The name of her last album was “The Idler Wheel Is Wiser than the Driver of the Screw and Whipping Cords Will Serve You More than Ropes Will Ever Do.”

David Arquette vs. Paul Reiser

As a former WCW World Heavyweight Champion, you’d think David Arquette would have an advantage over Paul Reiser in a deathmatch. But you’re forgetting that Paul managed to survive for more than two thirds of the movie Aliens. David Arquette couldn’t even deal with Matthew Lillard and Skeet Ulrich in Scream.