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  • Acceptable Targets: Although she never fought on the show, Tara Reid and her breasts were mentioned a lot by Nick and Johnny in the revival.
  • Big-Lipped Alligator Moment: James Gandolfini's dream sequence during his match with Robert De Niro. Also Crosses the Line Twice.
    • Anytime the Masked Man appeared to interrupt a fight.
    • Dennis Franz making a cameo as the Ally McBeal Dancing Baby during the Lucy Lawless vs Calista Flockhart fight. It comes straight out of no where and adds nothing to the fight (Lucy gets distracted for a second, but Calista doesn't do anything to take advantage of the distraction). Even when Franz comes back later in a fight of his own, the only vague reference to it is that Mills Lane hates him "for some reason".
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    • Cindy Margolis in the Video Game, for some reason they made her into a cyborg/robot presumably because at the time she had such an overwhelming online presence … although that still barely makes any sense and is never really discussed.
  • Critical Research Failure:
    • An interesting case, as this show generally averts this trope and loves to exploit the minutiae of its combatants for comedy, yet there were two jarring mistakes made in the Buster Keaton vs. Charlie Chaplin match:
      • A: Fatty Arbuckle makes an appearance in the audience, and Johnny makes a comment that he will have a long, good career. However, if you know anything about Arbuckle, you'd know that in 1921 he was arrested for allegedly raping and killing a young actress at a party. Despite the fact that he was innocent, the controversy not only ruined his career, it and other Hollywood scandals were a major catalyst for the creation of The Hays Code in order to "clean up" the industry. This fight took place in 1928, long after his career had been destroyed.
      • B: Johnny makes a comment about how the train Keaton uses to win is from "[his] masterpiece, The General". The General, despite being considered a classic now, bombed when it came out in 1926, just two years before this fight.
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    • One episode had Benito Mussolini appearing and for some reason wearing a pickelhaube. Why an Italian would be wearing a German helmet from the First World War is not addressed.
    • The Conan O'Brien vs. Bill Maher fight has Maher begrudging O'Brien his Harvard education. Maher quips "C'mon Conan. You think only you Ivy Leaguers can come up with a pimp robot and a sock puppet that says 'poop'?"note  But in real life, Maher's alma mater was Cornell; he's an Ivy Leaguer himself.
    • In The Britney Spears vs. Christina Aguilera fight, the hosts claim that Aguilera's Spicy Latina roots are showing when she uses a move they call the "Brazilian Body Spear". Not only has Aguilera never lived in any part of Latin America, but her ancestry is Ecuadorian on her father's side, not Brazilian.
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  • Crosses the Line Twice: See Big-Lipped Alligator Moment above.
  • Ensemble Dark Horse: Stacy Cornbred, especially after her death, and even more so after the fan reactions to Debbie and Tally's Jerkass behavior. It was most likely the reason behind her coming back from the dead in a Season 3 Halloween episode (and the video game.)
  • Epileptic Trees: It was strongly implied that The Masked Man was Michael Jackson, as his pale skin, high-pitched voice, eccentric dance moves, and habit of seductively leering at little boys (often distracting him long enough to allow the other guy to get a hit in, causing him to flee screaming) were all dead giveaways. Despite this, nobody could ever quite figure out who he was.
  • "Funny Aneurysm" Moment: The show hasn't aged well, given what happened to the celebrities featured in Real Life. Some examples:
    • In the Penn & Teller vs. Siegfried and Roy fight, a tiger is used as a weapon at one point. Since Roy's real-life mishap with the tiger that brought their show to an end, parodies in which their tiger goes berserk just don't seem quite as funny, even if everyone knew it would one day be a reality. (That includes the one on the Simpsons episode where Springfield legalizes gambling and Mr. Burns opens his own casino.)
    • During their fight, Medusa tail-whips Steve Irwin in the chest and sends him out of the ring. Once he recovers, he reaches inside the wound, holds his heart out, and then puts it back in its place, saying "What a stinger!" Yeah, not so funny now that Irwin's death was caused by a stingray inflicting a fatal chest wound (and, not, as other shows have predicted, by being eaten by a crocodile).
    • The Game getting shot by 50 Cent became less funny when it was revealed that The Game's brother actually had been shot shortly before the fight. The Game's father even criticized MTV for airing that episode.
    • The Artist Formerly Known as Prince dying against The Prince Formerly Known as Charles with the help of Queen Elizabeth II is this now that Prince ended up dying on the same day as the Queen's 90th birthday.
    • Brandy unintentionally killing Courtney Love was a bit painful to watch after the real-life Brandy accidentally killed someone in a car accident.
    • The appearance of Adam West had a running gag of him being dead and brought back with the Time Machine despite his insistence he's not dead. This joke isn't funny anymore since Adam passed away from leukemia.
    • In the Billy Crystal vs. Robin Williams vs. Whoopi Goldberg fight, Whoopi bisects Robin while having him in a choke hold. This is a lot harder to watch after his suicide via hanging in 2014.
    • The very disrespectful rematch between Shaq and Kobe Bryant, which was less a fight and more a way to give a Take That, Scrappy! towards Bryant after allegations of rape. In addition to being exonerated of those accusations, he and his daughter died tragically in a helicopter crash in 2020.
    • In the "Deathbowl '98" pilot episode that features RuPaul vs. Pamela Anderson, RuPaul asks, "Are there any time-outs in case one of us has to use the ladies' room?", and Pamela responds, "Don't you mean the men's room?!" Nearly 20 years later, when transgender rights entered the mainstream discussion, and bathroom laws are becoming widespread in North Carolina, Mississippi, and other states, the fights over which genders should use which bathrooms are turning into clashes and wars, with one side (the LGBT community and LGBT rights groups) claiming that not allowing transpeople to use bathrooms based on gender identity is discrimination and a violation of privacy, and the other side (the religious right groups and Moral Guardians) claiming that allowing transpeople into bathrooms based on gender identity violates religious freedom and would empower crossdressing rapists. The "bathroom wars" are still escalating as of 2016.
  • Hilarious in Hindsight:
    • In two separate matches, Al Gore kills "Weird Al" Yankovic, and Bush frontman Gavin Rossdale kills George W. Bush. In the 2000 Presidental Election, Bush defeated Gore (though this is a "Funny Aneurysm" Moment if you voted for Gore and/or had no idea that George W. Bush actually would win). (Bush shows up alive in a later episode after the election.)
    • The fight between Leonardo DiCaprio and Jack Nicholson is funnier when you realize that they both starred in The Departed.
      • The whole premise of that fight counts. At the time, Titanic (1997) had just come out and everyone expected Leo to be the next flash-in-the-pan pretty boy. Yeah, you see, about that...
    • In the Britney Spears vs. Christina Aguilera match, Christina has her hair ripped off when she throws Britney (who was tied to her hair) out of the ring, leaving her bald. Kinda ironic, considering that Spears would be the one who ended up bald when she went on her infamous meltdown between 2006 and 2007.
    • In the Nicolas Cage vs. John Travolta fight (which referenced their film Face/Off by literally switching their faces), Cage slathered Travolta's face in honey and allowed bees to attack him. No points guessing why this is hilarious.
    • A decade or so ago, during the Time Travel episode, there was a fight between Sherlock Holmes and Jack the Ripper. Today, there is this...
    • During the fight between David Arquette and Paul Reiser, David's sister Rosanna calls him, demanding to be in Scream 4. David's response? "Rosanna, I told you: 'No more Scream movies!'" And in comes 2011...
    • Chuck Norris getting sliced in half with one kick by Jean-Claude Van Damme (who was supposed to fight Jackie Chan; Norris was just a guest referee) becomes hysterical in light of the Chuck Norris Facts.
    • The fight between Mary-Kate and Ashley Olsen is won by the "third Olsen twin", a hideously deformed Madwoman in the Attic who eats them both. Today, Elizabeth Olsen has easily eclipsed her older sisters in terms of her career, becoming a critically acclaimed actress in indie films like Martha Marcy May Marlene and Liberal Arts with a Hollywood Hype Machine push in front of her, playing Wanda Maximoff in the Marvel Cinematic Universe.
    • During the fight between Winona Ryder and Gwyneth Paltrow, Johnny at one point calls Winona a "little pepper pot". Pretty ironic, considering how Gwyneth was the one who went on to play Pepper Potts in the Iron Man films.
    • The Tony Bennett/Willie Nelson match became this in the following decade, when Nelson would perform "On the Sunny Side of the Street" alongside Bennett for the latter's Duets II album.
    • Mills Lane fighting Judge Judy became this after Lane later went on to host his own courtroom TV series.
    • One episode has J. K. Rowling fighting Stephen King, with Rowling being derided for having no idea how to kill someone because she's only a children's author. This was before the Harry Potter series became notorious for the body count that accumulated in the later books.
    • "Censorship Problems" (Season 2, Episode 22, original airdate July 15, 1999), featured Alanis Morissette defeating Jewel in a ladder match for charity. After the match, Alanis celebrated by randomly stripping naked (a Parody of her then-current "Thank U" video), though with Godiva Hair and Hand-or-Object Underwear. Seven months later, on December 12, 1999 at WWF Armageddon 99, Miss Kitty defeated WWE Women's Champion Ivory, Jacqueline and B.B. in a Four-Way Evening Gown in a Pool Match for the title. After the match, she celebrated by stripping off her gown and jumping into the pool. She then removed her bra and flashed her breasts, marking the first example of intentional nudity on a PPV.note 
    • During the Prince vs. Prince Charles match, Prince Charles attacks his mother, Queen Elizabeth II, saying that it's his turn to be king, and the Queen retaliates and says "Over my dead body!" Now that Elizabeth II has become the longest-reigning monarch in British history (with some even believing she may outlive Prince Charles) this becomes even funnier.
    • When Don King enters the ring in his battle with Donald Trump, he’s wearing an American flag-patterned outfit while a rock version of “The Star-Spangled Banner” plays, because “only in America can a convicted killer become a millionaire”. Funnily enough, it was his opponent that would end up being in charge of the USA.
    • The fight between Missy Elliott and Beyoncé (which was made when Beyoncé was still a member of Destiny's Child) concludes with Missy opening the "Mystery Box of Fun" to reveal a beehive inside of it, and getting stung to death by bees, leaving Beyoncé as the winner. Considering Beyoncé's Fan Community Nickname is "The Beyhive", this becomes even more fitting for modern audiences.
    • In the episode "Where is Stallone?" Johnny mentions that it's amazing that no one had ever made a movie starring both Sylvester Stallone and Arnold Schwarzenegger. Twelve years later, The Expendables, the first film ever to star both Stallone and Schwarzenegger, came out. As an added bonus, The Expendables also stars "Stone Cold" Steve Austin, who made his first CDM appearance in that very episode.
    • At the end of the episode "Fourth of July Celebration", Nick's pretense of having been in The Vietnam War is uncovered by some real Vietnam veterans. When Nick insists that he was "in Vietnam, fighting Charlie", one of the veterans says "The only Charlie you've ever seen in Vietnam is Charlie Sheen!" Come the next episode, "Family Night I", and guess who's competing in the first match?
    • The match between Tobey Maguire and Jake Gyllenhaal in "The Beginning of Celebrity Deathmatch" is extra hilarious now that Gyllenhaal has gone up against a different Spider-Man. For bonus points, he won both times (killing Maguire in the death match and pulling off a Thanatos Gambit in the film).
  • Ho Yay: Nick Diamond and his extensive knowledge regarding "back massagers"note  during the Sex in the City deathmatch. Apparently Nick just has a really, really bad back.
  • Jerkass Woobie:
    • Genghis Khan in his match against Mahatma Gandhi, while it was not hard to feel bad for the guy while Gandhi brutally humiliated and tortured him to death, one not only has to remember Khan was a horrible and bloodthirsty invader in his own time, but the only reason the fight went the way it did was because Genghis and Gandhi's personalities were swapped on the way through the time machine, so everything that happened to him he would have happily inflicted onto poor Gandhi if he had come through with his own mind intact.
    • Tommy Lee could also count in the latter two of his three appearances, especially his final fight against Pamela Anderson. He spent the entire fight egging his ex on so she would kick his ass only to prove the point that he has changed for the better and despite getting beat up he wouldn't hit her again. Pamela counters that although she can see Tommy Lee has changed, so had she, and she kills him to prove she's moved on with her life.
  • Moe: Stacy has her moments. Look at that smile!
  • More Popular Spin-Off: This show originated from Cartoon Sushi.
  • The Problem with Licensed Games: A pitifully short roster, career mode, create-a-celebrity, weak controls, etc. will mean you will do everything possible in the game within two hours.
  • Replacement Scrappy: Debbie Matenopoulos and Tally Wong for Stacy Cornbred.
  • Seasonal Rot: Though some feel that the show jumped the shark when Stacy Cornbred was killed off, the later episodes of the original run were still considered far superior to the revival that aired on MTV2's Sick-a-Mation lineupnote , which was so bad it's considered Fanon Discontinuity. The reason? Eric Fogel wasn't executive producer.
  • Special Effect Failure: When Tally Wong frowns, her lips are merely turned upside down. It's rather obvious.
  • Squick:
  • What an Idiot!: Little Richard tearing off his own nipples and bleeding to death in his fight against Lil' Kim.note 
    • Nick Lachey manages to out-idiot Jessica Simpson. She gives him a grenade with the pin still in it, but then he pulls the pin and holds it, blowing himself up.
  • Woolseyism: Due to the extensive use of puns and American idioms, most foreign translations have to adapt some jokes:
    • When Mankind fought against Ernest Hemingway, the latter says when the former was being strangled by the ring rope that he is going to get out "The easy way or the Heming-way", a pun from the idiom My way or the highway. Since there's no way to translate the joke literally, the Latin American Spanish subs translated the joke as A la manera dificil o la mia (The hard way or my way, in this case, Hemingway's).

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