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Season guide

Celebrity Deathmatch: Season 2

21 episodes Premiered Jan 31, 1999 Updated Oct 7, 2026
Previously on Celebrity Deathmatch

Season 2 Lore Primer

Key plot threads, lore context, and character stakes you need to remember before diving into this season.

  • ⚡ Picks up essential narrative continuity directly following the events of Celebrity Deathmatch Season 1.
  • ⚡ Character alliances, factions, and personal loyalties undergo significant shifts under escalating stakes.
  • ⚡ Addresses unresolved cliffhangers and thematic mysteries introduced during previous seasons.
  • ⚡ Establishes the primary seasonal conflict that drives serialized character arcs toward the finale.
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Season 2 Episodes

Episode Guide

🛡️ SPOILER SHIELD

Season 2 Progress Shield

Future titles & synopses blurred. Tap "Reveal" on any card to peek.
Binge Efficiency Engine

Season 2: Filler vs. Essential Canon

Filter episodes by narrative weight. Focus on essential mytharc and skip standalone side quests.

19%
81%
Mytharc (4): Crucial lore & season climaxes
Core (17): Character development & subplots
Side Quest (0): Standalone / filler
S2·E1 Mytharc

Deathbowl '99

Jan 31, 1999

1. Dolly Parton vs. Jennifer Lopez 2. Madonna vs. Michael Jackson 3. Mike Tyson vs. Evander Holyfield

S2·E2 Core

The Battle of Boys With Toys

Feb 4, 1999

1. Ice Cube vs. Ice-T 2. Robert DeNiro vs. Al Pacino 3. Backstreet Boys vs. Beastie Boys

S2·E3 Core

Magic, Flashbacks and Pregnancies

Feb 11, 1999

1. Calista Flockhart vs. Lucy Lawless 2. Boy George vs. Don Johnson 3. Penn & Teller vs. Siegfried & Roy

S2·E4 Core

The Time Machine

Feb 18, 1999

1. Jennifer Aniston vs. Courteney Cox vs. Lisa Kudrow 2. Sean Connery vs. Roger Moore 3. Gandhi vs. Genghis Khan

S2·E5 Core

The Unknown Murderer

Feb 25, 1999

1. Moses vs. Pharaoh 2. Larry King vs. Geraldo Rivera 3. Neve Campbell vs. Sarah Michelle Gellar

S2·E7 Core

The End of the Real World

Mar 11, 1999

1. Kate Moss vs. Claudia Schiffer vs. Tyra Banks 2. William Shakespeare vs. Busta Rhymes 3. The Real World's: Puck vs. Jon vs. Tami vs. Jacinda

S2·E8 Core

Celebrity Deathmatch - The Motion Picture

Apr 22, 1999

It features fights that are about the elements of movies. The fights are Martin Scorsese vs. Oliver Stone in Fight 1, Fight 2 is Groucho Marx vs. John Wayne, and the Main Event is

S2·E9 Core

Cable Day

May 6, 1999

1. Emeril Lagasse vs. The Two Fat Ladies 2. Matt Pinfield vs. Jesse Camp 3. Alex Trebek vs. Pat Sajak

S2·E10 Core

4th of July Celebration

Jul 1, 1999

1. Bill Clinton vs. Kenneth Starr 2. James Van Der Beek vs. Saddam Hussein 3. Abe Lincoln vs. George Washington

S2·E11 Core

Family Night I

Jul 8, 1999

1. Charlie Sheen vs. Emilio Estevez 2. Eric & Julia Roberts vs. Donny & Marie Osmond 3. Bob & Jakob Dylan vs. Jerry & Ben Stiller

S2·E12 Core

Censoring Problems

Jul 15, 1999

1. Tommy Lee vs. Ron Jeremy 2. Alanis Morissette vs. Jewel 3. The Three Stooges vs. The Three Tenors

S2·E13 Core

Salute to Laughter

Jul 22, 1999

It's comedian time! 1. Dennis Miller vs. Carrot Top 2. Rodney Dangerfield vs. Don Rickles Main Event: Billy Crystal vs. Robin Williams vs. Whoopi Goldberg

S2·E14 Core

The Laser Pointer

Jul 29, 1999

1. Elton John vs. Ozzy Osbourne 2. Martha Stewart vs. Sandra Bernhard Main Event: Tom Hanks vs. Sean Penn

S2·E15 Core

Robot Nicky

Aug 5, 1999

1. Ricky Schroder vs. Gary Coleman 2. Lauryn Hill vs. Shania Twain 3. Hugh Grant vs. All-comers [ Clint Eastwood, Harvey Keitel, & Andy Dick ]

S2·E16 Mytharc

The Prophecy

Oct 7, 1999

1. Dennis Franz vs. Sammo Hung 2. Steven Wright vs. Chris Tucker 3. Gwyneth Paltrow vs. Winona Ryder

S2·E17 Core

In The Memory Of Stacy Cornbred

Oct 14, 1999

1. Cher vs. Bette Midler 2. Benito Mussolini vs. Roberto Benigni 3. John Travolta vs. Nicolas Cage

S2·E18 Core

From The Streets Of New York

Oct 21, 1999

In this episode, the deathmatch cast interviews people in New York, about which fights they want to see.

S2·E19 Core

Halloween Episode I

Oct 28, 1999

1. Frankenstein's Monster vs. The Wolfman 2. Captain Doody vs. The Undertaker 3. 'N Sync vs. Kiss

S2·E20 Mytharc

High Tech Fighting

Nov 4, 1999

1. Richard Simmons vs. Billy Blanks 2. Don King vs. Donald Trump 3. Brad Pitt vs. Keanu Reeves

S2·E21 Mytharc

Fandemonium II

Nov 11, 1999

1. Ben Affleck vs. Matt Damon 2. Ozzy Osbourne vs. Rob Zombie 3. Marilyn Manson vs. Ricky Martin

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