"It's a typical erogenous zone match-up. But remember, Dolly may have a sizable advantage - she's got two T's. Jennifer, no matter how big it is, has only one A."
—Dr. Ruth Westheimer
The first episode of the second season of Celebrity Deathmatch, known as Deathbowl '99.
This episode consists of two pre-determined fights and one half-time performance. The first undercard fight features Dolly Parton and Jennifer Lopez showing off their huge assets. The half-time show from Madonna is interrupted by a show-stealing Michael Jackson. The second fight and main event features a rematch between heavyweight boxing stars Mike Tyson and Evander Holyfield.
This episode contains examples of:
- Acid Pool: When Madonna and Michael Jackson's fight is made official, the ring is surrounded by a pool of hydrochloric acid.
- Ass Kicks You: Jennifer Lopez wears special armor that allows her to utilize her buttocks as a weapon during her fight.
- Boxing Battler: Both Mike Tyson and Evander Holyfield.
- The Cameo: This episode features an appearance from Dr. Ruth Westheimer.
- Camera Abuse: Mike Tyson repeatedly slams Evander Holyfield's face into one of the camera during their fight. What makes this interesting is that we first see it from said camera's perspective, before switching to another shot that shows the cameraman standing there while Mike is still slamming Evander's face into it.
- Combat Pragmatist: Mike Tyson quite literally distracts Evander Holyfield with all sorts of red herrings, ranging from a fake phone call to claiming that Evander's wife is waiting for him back home and looks very angry at him.
- Dance Battler: To be expected with Michael Jackson, however both he and Madonna also face off in a crotch-grabbing contest quite early on in their fight.
- Drill Sergeant Nasty: Jennifer Lopez's personal trainer from her Training Montage is one of these.
- Explosive Decompression: Dolly Parton is launched into outer space with Jennifer Lopez's buttocks, where she promptly explodes.
- Funbag Airbag: Quite early in the fight, Jennifer Lopez trips Dolly Parton, however the latter is able to use her breasts to not only cushion the fall but to also bounce her back up.
- Hoist by His Own Petard: Michael Jackson uses his Moonwalker magic to transform himself into what was meant to be some sort of deadly creature. Instead, he transforms into a hamster without realizing.
- Interrupted Intimacy: After their fight spills out of the arena, Mike Tyson and Evander Holyfield crash into a couple's bedroom while they are about to get intimate.
- Magic Plastic Surgery: After being knocked into the Acid Pool, Michael Jackson is able to climb back out almost completely unscathed. The acid somehow has an effect with the plastic surgery that manages to undo his iconic transformation, and we see what Michael could have looked like has he just stuck with his original face.
- Male Gaze: At the beginning of the fight with Dolly Parton and Jennifer Lopez, Mills is seen quite obviously ogling Dolly's breasts before he starts the fight.
- Marshmallow Hell: Played with. Using her breast-enhancing battle gear, Dolly Parton is able to grab Jennifer Lopez by the face with her breasts and lift her off the ground.
- Noodle Incident: During their commentary of the first fight, Dr. Ruth mentions a conversation Nick had with her regarding a "stamina problem" in the bedroom.
- Phoney Call: One of the methods Mike Tyson uses to trick Evander Holyfield during their fight.
- Plunger Detonator: The licensed demolition team that are planning on demolishing the building that Mike Tyson and Evander Holyfield are fighting on, use one of these.
- Randomized Transformation: Michael Jackson's ability to shapeshift using his Moonwalker magic seems to work in this fashion. While we don't know what he intended to turn himself into, we're pretty sure he didn't mean to turn himself into a hamster of all things.
- Rocket Punch: With the press of a button, Michael Jackson is able to launch his fist at Madonna.
- Self-Damaging Attack Backfire: Michael Jackson's Rocket Punch is easily dodged by Madonna, and it instead bounces off the rope behind her. It ends up punching Michael in the ricochet and knocks him into the Acid Pool outside the ring.
- Stuff Blowing Up: Mike Tyson manages to push Evander Holyfield off of a building...and right onto the detonator of a demolition team's explosives, causing said building to explode along with Tyson.
- Super Gullible: Evander Holyfield is portrayed as this, falling for literally every distraction Mike Tyson throws at him.
- Training Montage: Prior to the first fight, we are shown a training montage for both Dolly Parton and Jennifer Lopez to ensure their assets are in top fighting condition.
