In 1998, Celebrity Deathmatch, an animated series featuring caricatures of celebrities engaging in professional wrestling, made its debut on MTV. The show quickly became one of the most popular shows on the music network because of the gore, and commentary.

Created by Eric Fogel and first appearing on Cartoon Sushi, Celebrity Deathmatch's first bout pitted convicted murderer Charles Manson against rock star Marilyn Manson" and would later air a pilot episode featuring Kathie Lee Gifford taking on Howard Stern, Pamela Anderson against RuPaul and Spice Girls versus Hanson, during MTV's Super Bowl XXXII halftime special.

The success of the pilot would set the stage for Celebrity Deathmatch to enter MTV's main lineup, making its official debut on May 14, 1998. Hosted by fictional commentators Johnny Gomez and Nick Diamond, as well as referee Mills Lane, Celebrity Deathmatch would poke fun at pop culture throughout its initial four-season run, with celebrities in entertainment and beyond being thrust into the ring to fight each other to the death. Arriving at a time when hip-hop and r&b were dominating the charts and its stars were becoming household names, it was only right that Celebrity Deathmatch embraced the culture.

After airing 75 episodes, the first incarnation of Celebrity Deathmatch ended when the show was canceled in 2002, but the show would be revived in 2005, with the season 5 premiere airing on June 10, 2006. Produced without any involvement by creator Eric Fogel, Celebrity Deathmatch would run for two more seasons before the plug was pulled on the show again in 2007, ending its run as an iconic and influential show

In celebration of the 20th anniversary of its premiere, The Boombox looked back on some of the most memorable moments involving hip-hop and r&b in MTV Celebrity Deathmatch history.

  • 1

    Mariah Carey vs. Jim Carrey

    On the first episode of MTV's Celebrity Death Match ever, R&B superstar Mariah Carey faced off against actor Jim Carrey to determine who was the rightful owner of the name. In the end, Mariah's high octave would blow Carrey's mind, literally, and score her the victory, which came off the heels of her fourth studio album, Butterfly.

  • 2

    Puff Daddy vs. Trent Reznor

    One accolade that often gets overlooked in Diddy's career is him being the first rapper to ever appear on an episode of Celebrity Deathmatch. Facing off against Nine Inch Nails founder Trent Reznor, the artist formerly known as Puff Daddy would be deemed the victor of the match, but would also meet his own demise after being sliced to death himself by Trent Reznor's fingernails.

  • 3

    Brandy Norwood vs. Courtney Love

    During the '90s, r&b singer Brandy Norwood was known as one of America's sweethearts and the prototypical girl next door, so it was only right that Celebrity Deathmatch put her in the ring against Courtney Love, one of the most controversial rockers of the decade. Brandy Norwood would attempt to make peace by offering Courtney a bear, but the gift would prove to be a Trojan horse, as Love would be mauled by the bear, giving Brandy the win by default.

  • 4

    Ice Cube vs. Ice-T

    Two of the preeminent voices in west coast hip-hop locked horns when Ice Cube and Ice-T were pitted against each other during the second season of MTV Celebrity Deathmatch to determine who was the better "Ice." Set in an actual skating rink and featuring a cameo from Vanilla Ice, the match would end with Ice Cube as the victor, making it yet another good day for the former N.W.A. frontman.

  • 5

    Busta Rhymes vs. William Shakespeare

    A blast from the past is an understatement when looking back at Busta Rhymes'  Celebrity Deathmatch against William Shakespeare during season two. While Busta usually reigns supreme in a lyrical battle royal, in this instance, his decision to run into the time machine results in him being transported to the past, making Shakespeare the winner by default.

  • 6

    Lauryn Hill vs. Shania Twain

    A cultural clash occurred when MTV Celebrity Deathmatch pit Lauryn Hill against Shania Twain, two of the most acclaimed female soloists of the '90s. Lauryn Hill's arsenal of weapons would prove too much for the country star, who would ultimately take the L in this memorable match-up.

  • 7

    TLC vs. Dixie Chicks

    Carnage ensues when TLC and the Dixie Chicks become entangled in a battle royal during the third season of MTV Celebrity Deathmatch. TLC was named the victors after Lisa "Left-Eye" Lopes is the last fighter left standing, but the rapstress gets hacked to pieces by Lucy Lawless, who makes her return during this memorable episode.

  • 8

    Diana Ross vs. Whitney Houston

    Two of the greatest divas of the past century collided during the third season of MTV Celebrity Deathmatch when Motown icon Diana Ross squared off against her R&B heir Whitney Houston. When the dust cleared, Whitney Houston would walk away from the match as the sole survivor, as Diana Ross' head would be burnt to a crisp, but not before doing her own share of damage to an unsuspecting security guard.

  • 9

    Ol' Dirty Bastard vs. LeAnn Rimes

    One of the more odd pairings in MTV Celebrity Deathmatch history was Wu-Tang Clan's wild-man Ol' Dirty Bastard and country music's sweetheart LeAnn Rimes. ODB may have famously let the world know Wu-Tang was for the kids while crashing the Grammy's in 1998, however, no mercy would be given to the teenage star, who would catch the blues she sang about in ways unimaginable.

  • 10

    Lil' Kim vs. Little Richard

    Pianist and composer John Tesh is the guest commentator of the bout between Lil Kim and Little Richard, two of the more flamboyant style icons of all time. Little Richard may have gotten cheated out of his rightful props as the inventor of rock-n-roll, but loses this fight fair and square, as Lil Kim morphed into Dr. Lil Kim, and gave Richard a makeover.

  • 11

    Beyoncé vs. Missy Elliott

    One of the premiere showdowns of the fourth season of MTV Celebrity Deathmatch was the fight between then Destiny's Child member Beyoncé and rising superstar Missy Elliott in a ladder match. Featuring cameos from Beyonce's father, Mathew Knowles, as well as Mr. T, the soon-to-be soloist would be deemed the victor after Missy Elliott was stung to death by bees after reaching the mystery box at the top of the ladder.

  • 12

    LL Cool J vs. Queen Latifah

    LL Cool J and Queen Latifah were among the first rap acts to successfully transition into careers as actors, but the two would first cross paths on screen as contestants on MTV's Celebrity Deathmatch. Locking horns in a ring that resembled the set of The Queen Latifah Show, LL, and the Queen would go blow for blow 'til the bitter end. Cool James would be sliced up like one of his classic records in a loss, proving once again that ladies are first, especially when Latifah is around.

  • 13

    Lil Jon vs. Lil' Flip and Lil' Bow Wow

    "King of the Lil' People," one of the more rap-centric episodes to air during Celebrity Deathmatch's six-season run, would feature appearances from the likes of Lil Wayne, Lil' Bow Wow, Lil' Flip, Lil' Romeo and Lil Jon. All five men stepped into the ring in a mini tourney. In the end, Lil' Bow Wow would defeat Lil' Romeo and Lil Wayne would fall short, and lose to  Lil' Flip, resulting in a face-off between Bow Wow and Flip for the ultimate bragging rights. However, both would challenge Lil Jon to a match after catching wind of him proclaiming himself as "King of the Lil' People," but would ultimately eat their words, with Lil Jon emerging as the victor.

  • 14

    Rev Run vs. Russell Simmons

    The spiritual met the secular when Run-D.M.C. member Rev Run and hip-hop mogul Russell Simmons go toe-to-toe during the sixth season of MTV Celebrity Deathmatch. The two pioneers put their brotherly love aside for this battle, which Rev Run wins with a roundhouse kick that decapitates his older brother.

  • 15

    50 Cent Vs The Game

    One of the few instances in which a beef that first occurred off wax making its way to MTV Celebrity Deathmatch was the rift between G-Unit members 50 Cent and The Game, who stepped in the ring to settle the score during the show's sixth season. While The Game would put up a respectable fight, 50 Cent's nine bullet-wounds would be the deciding factor, making him the last rapper to win a match before MTV Celebrity Deathmatch's would end its run.