* BigLippedAlligatorMoment:
** Creator/JamesGandolfini's dream sequence during his match with Creator/RobertDeNiro. Also CrossesTheLineTwice.
** Anytime the Masked Man appeared to interrupt a fight.
** Creator/DennisFranz making a cameo as the ''Series/AllyMcBeal'' Dancing Baby during the Creator/LucyLawless vs Creator/CalistaFlockhart fight. It comes straight out of nowhere 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".
** In the Wrestling/TheUndertaker vs Captain Doody[[note]] a demon possessing Nicky Jr.[[/note]] fight, Captain Doody suddenly turns into Creator/BobSaget. Apart from frightening Nick and Johnny telling him it’s only an allusion, this served no point in the fight.
** in the middle of the [[Series/{{Wildboyz}} Steve-O]] vs [[Series/TheAndyMilonakisShow Andy Milonakis]] fight, Milonakis is revealed to have the powers of the imagination, as shown when he uses a lightswitch to make Steve-O and Johnny disappear and reappear. This does nothing to help him in the fight [[spoiler: and he won by eating Steve-O [[MakesJustAsMuchSenseInContext who decided to dress up as a Twinkee]]]]
* EnsembleDarkhorse: Stacy Cornbred, especially after her death, and even more so after the fan reactions to [[ReplacementScrappy 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)''.
* EpilepticTrees: It was strongly implied that The Masked Man was Music/MichaelJackson, as his pale skin, high-pitched voice, eccentric dance moves, and [[MemeticMolester 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.
* HarsherInHindsight: This is going to happen with a show where celebrities are killed, but is especially acute if said celebrity meets an unnaturally early end in RealLife, or even if the circumstances of said death are a bit too close to what happened in the show. Some examples:
** In the Creator/PennAndTeller 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 [[WesternAnimation/TheSimpsons other]] [[Series/{{MADtv}} shows]] have predicted, by being eaten by a crocodile).
** [[{{Music/Prince}} The Artist Formerly Known as Prince]] dying against [[UsefulNotes/TheBritishRoyalFamily The Prince Formerly Known as Charles]] with the help of [[UsefulNotes/ElizabethII Queen Elizabeth II]] is this now that Prince ended up dying on the same day as the Queen's 90th birthday.
*** Speaking of that match, Prince Charles attacks his mother, saying that it's his turn to be King, and the Queen retaliates and says "Over my dead body!" Elizabeth II passed away in September 2022 with Charles becoming King.
** Music/{{Brandy}} unintentionally killing Music/CourtneyLove was a bit painful to watch after the real-life Brandy accidentally killed someone in a car accident.
** The appearance of Creator/AdamWest 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 Creator/BillyCrystal vs. Creator/RobinWilliams vs. Creator/WhoopiGoldberg 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 Creator/ShaquilleONeal and Kobe Bryant, which was less a fight and more a way to give a TakeThatScrappy 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. Creator/PamelaAnderson, [=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 UsefulNotes/{{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 trans people to use bathrooms based on gender identity is discrimination and a violation of privacy, and the other side (the religious right groups and MoralGuardians) claiming that allowing trans people into bathrooms based on gender identity violates religious freedom and would empower [[CreepyCrossdresser crossdressing rapists]]. The "bathroom wars" are still escalating as of 2022. Not to mention that nowadays deliberately misgendering a trans person is considered offensive and ignorant towards them.
** The fight between Creator/CoreyFeldman and Creator/CoreyHaim, where they were fighting for the chance to work with Harvey Weinstein. Essentially, two victims of sexual abuse as minors, fighting over an opportunity to work with a notorious instigator of sexual abuse. Even worse is that, very early on in the fight, one of Feldman's attacks on Haim (severely scratching his back with the studs on the front of his leather jacket) is deliberately animated in a way that makes it look like Feldman is...doing something grossly inappropriate...to Haim. [[WordOfGod Eric Fogel]] went on record many years later to state that this was his least favorite fight of the original series.
** In "Assamania I", Nick does a bunch of '' Series/{{Jackass}} '' stunts as he fears that '' Jackass'''s higher ratings will get their show canceled. The episode was the penultimate episode of the original series's final season.
* HilariousInHindsight:
** In two separate matches, UsefulNotes/AlGore kills Music/WeirdAlYankovic, and Bush frontman Gavin Rossdale kills UsefulNotes/GeorgeWBush. In the 2000 Presidental Election, Bush defeated Gore (it's also HarsherInHindsight if you voted for Gore and/or had no idea that UsefulNotes/GeorgeWBush actually would win). (Bush [[UnexplainedRecovery shows up alive]] in a later episode after the election.)
** The fight between Creator/LeonardoDiCaprio and Creator/JackNicholson is funnier when you realize that they both starred in ''The Departed''.
*** The whole premise of that fight counts. At the time, ''Film/{{Titanic 1997}}'' had just come out and everyone expected Leo to be the next flash-in-the-pan pretty boy. [[Film/TheDeparted Yeah]], [[Film/TheAviator you]] [[Film/BloodDiamond see]], [[Film/DjangoUnchained about]] [[Film/TheWolfOfWallStreet that]]...
** In the Music/BritneySpears vs. Music/ChristinaAguilera 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 Creator/NicolasCage vs. Creator/JohnTravolta fight (which referenced their film ''Film/FaceOff'' by ''literally'' switching their faces), Cage slathered Travolta's face in honey and allowed bees to attack him. [[Film/TheWickerMan2006 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 [[VideoGame/SherlockHolmesVersusJackTheRipper 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!'" [[Film/{{Scream 4}} And in comes 2011...]]
** Creator/ChuckNorris getting [[OneHitKill sliced in half with one kick]] by Creator/JeanClaudeVanDamme (who was supposed to fight Creator/JackieChan; Norris was just a guest referee) becomes hysterical in light of the Website/ChuckNorrisFacts.
** The fight between Creator/MaryKateAndAshleyOlsen is won by the "third Olsen twin", a hideously deformed MadwomanInTheAttic who [[ImAHumanitarian eats them both]]. Today, Creator/ElizabethOlsen has easily eclipsed her older sisters in terms of her career, becoming a critically acclaimed actress in indie films like ''Film/MarthaMarcyMayMarlene'' and ''Film/LiberalArts'' with a HollywoodHypeMachine push in front of her, playing [[ComicBook/ScarletWitch Wanda Maximoff]] in the Franchise/MarvelCinematicUniverse.
*** Furthermore, the "third Olsen twin"'s name is said to be Betty Sue Olsen. What is the name "Betty" traditionally short for? ''Elizabeth''!
** During the fight between Creator/WinonaRyder and Creator/GwynethPaltrow, 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 ''Film/IronMan'' films.
** The Tony Bennett[=/=]Music/WillieNelson 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 Creator/JKRowling fighting Creator/StephenKing, with Rowling being derided for having no idea how to kill someone because she's only a children's author. This was before the ''Franchise/HarryPotter'' 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 Music/AlanisMorissette defeating Music/{{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 GodivaHair and HandOrObjectUnderwear. ''Seven months later'', on December 12, 1999 at ''[[Wrestling/ArmageddonWWE WWF Armageddon]] 99'', [[Wrestling/StacyCarter Miss Kitty]] defeated [[http://www.wrestling-titles.com/wwe/wwf-wm.html WWE Women's Champion]] Wrestling/{{Ivory}}, Wrestling/{{Jacqueline}} and [[Characters/WWEDivas B.B.]] in a [[GimmickMatches Four-Way Evening Gown in a Pool Match]] for the title. After the match, she celebrated by stripping off her gown and [[SexySoakedShirt jumping into the pool]]. She then removed her bra and flashed her breasts, marking the first example of intentional nudity on a PPV.[[note]]Apparently, she was supposed to have been shown from the back, but someone hit the wrong button and her breasts went out to the world.[[/note]]
** When Don King enters the ring in his battle with UsefulNotes/DonaldTrump, he’s [[WearingAFlagOnYourHead 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 [[UsefulNotes/DonaldTrump his opponent]] that would end up being ''in charge'' of the USA.
** The fight between Music/MissyElliott and Music/{{Beyonce}} (which was made when Beyoncé was still a member of Music/DestinysChild) 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 FanCommunityNickname 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 Creator/SylvesterStallone and Creator/ArnoldSchwarzenegger. Twelve years later, ''Film/TheExpendables'', the first film ever to star both Stallone and Schwarzenegger, came out. As an added bonus, ''The Expendables'' also stars Wrestling/StoneColdSteveAustin, who made his first CDM appearance in that very episode.
** At the end of the episode "Fourth of July Celebration", Nick's [[PhonyVeteran pretense of having been in]] UsefulNotes/TheVietnamWar 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 [[Film/{{Platoon}} Charlie Sheen]]!" Come the next episode, "Family Night I", and [[Creator/CharlieSheen guess who's competing in the first match]]?
** The match between Creator/TobeyMaguire and Creator/JakeGyllenhaal in "The Beginning of Celebrity Deathmatch" is extra hilarious now that Gyllenhaal has [[Film/SpiderManFarFromHome gone up against a different Spider-Man]]. For bonus points, [[spoiler:he won both times (killing Maguire in the death match and pulling off a ThanatosGambit in the film).]]
*** The whole joke of the Tobey vs. Jake fight is that the two look and act so similar that people have a hard time telling them apart. Come 2009, and the two are starring as siblings in the film ''Film/Brothers2009''.
** Creator/AlfredHitchcock and Creator/StevenSpielberg would battle again 14 years later [[WebVideo/EpicRapBattlesOfHistory on a different stage]].
** Music/FaithHill kills Music/JanetJackson by grabbing her chest from behind and ripping the flesh from the front half of her torso. At the 2004 UsefulNotes/SuperBowl halftime show, a ''very similar thing'' happens to her, courtesy of Music/JustinTimberlake and a rather unfortunate WardrobeMalfunction...
* HoYay: Nick Diamond and his extensive knowledge regarding "back massagers"[[note]]giant dildos[[/note]] during the ''Sex in the City'' deathmatch. Apparently Nick just has a really, ''really'' bad back.
* JerkassWoobie:
** 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 [[http://img1.wikia.nocookie.net/__cb20121223195542/deathmatch/images/1/13/Stacycindy.png smile!]]
* MorePopularSpinoff: This show originated from ''WesternAnimation/CartoonSushi''.
* TheProblemWithLicensedGames: 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.
* ReplacementScrappy: Debbie Matenopoulos and Tally Wong for Stacy Cornbred.
* SeasonalRot: 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 lineup[[note]]Which also included other short-lived shows like ''Where My Dogs At'' and ''Pedro and Flocko'', and reruns of ''WesternAnimation/BeavisAndButthead'' and ''3 South''.[[/note]], which was so bad it's considered FanonDiscontinuity. The reason? Eric Fogel wasn't executive producer.
* SpecialEffectFailure: When Tally Wong frowns, her lips are merely turned upside down. It's rather obvious.
* {{Squick}}:
** Barbara Bush taking off her panties for Gavin Rossdale.
** [[Music/TheWhiteStripes Jack and Meg White]] going down and having sex on the ring mat, when it was still unclear whether they were exes or siblings.
** Speaking of siblings, Creator/AngelinaJolie’s brother James repeatedly coming on to her during her fight with Creator/SandraBullock.
** Some of the deaths on this show could fall under this territory, especially {{Music/Eminem}}, Creator/JimCarrey, Creator/KeriRussell, Colleen Haskell from {{Series/Survivor}}, and [[Creator/MaryKateAndAshleyOlsen Mary-Kate Olsen]] (in the revival).
* UnintentionalPeriodPiece:
** The show's original run is this to the late '90s and early '00s. From promoting tennis star Anna Kournikova and actress Elizabeth Hurley as the internet's top two pinups, to billing the long-separated Creator/BruceWillis[=/=]Creator/DemiMoore and Creator/TomCruise[=/=]Creator/NicoleKidman as two of Hollywood's biggest power couples (back before anybody knew who Creator/AshtonKutcher and Creator/KatieHolmes were), to featuring a fight between UsefulNotes/BillClinton and Kenneth Starr to finally settle the [[CaughtWithYourPantsDown Lewinsky scandal]], it is impossible for ''Celebrity Deathmatch'' to escape the turn-of-the-New-Millennium time period in which it aired. The show's pop culture reference-based humor grew dated fairly quickly, and many of the celebrities featured are now far past their fame. To children of the '00s and beyond who don't have a decent understanding of the minutiae of the era's pop culture, most of the jokes will fly over their head.
** The relaunch that aired on [=MTV2=] likewise dates itself to the mid-'00s. The first episode alone is built entirely around parodies of the long-canceled and largely forgotten reality shows ''The Simple Life'' and ''Series/VivaLaBam'', while other fights are about such TurnOfTheMillennium ephemera as ''Series/TheOsbournes'', ''Series/PimpMyRide'', [[Series/DaAliGShow Ali G]], {{crunk}} rap, Music/BritneySpears' and Creator/DaveChappelle's [[CreatorBreakdown public meltdowns]], and the [[UsefulNotes/{{Baseball}} Major League Baseball]] steroid scandal. One fight did reflect how the aforementioned Bruce Willis and Demi Moore had broken up... with the fight being between Willis and Ashton Kutcher, Demi's new lover (a relationship that ended in 2013), who was by then famous for hosting ''Series/{{Punkd}}''.
* {{Woolseyism}}: Due to the extensive use of puns and American idioms, most foreign translations have to adapt some jokes:
** When [[Wrestling/MickFoley Mankind]] fought against Creator/ErnestHemingway, 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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