After solving a riddle on an ancient space rock, Jimmy, Goddard, Carl, Sheen, Cindy, Libby, and Bolbi end up competing on a game show where the losers get their home planet destroyed. To save Earth, Jimmy must learn the importance of teamwork while being convinced by one of the rival teams to form an alliance to save the other planets as well.
"Win, Lose and Kaboom!" provides examples of:
- Back Blocking: At one point when fighting Meldar's robot army, the camera pans over to the right until April's mother's back fills the screen. Then the camera zooms out from, Meldar's assistant, Vandana's back.
- But Thou Must!: On Intergalactic Showdown, participation is mandatory and the teams must play all the way through; if they refuse to participate for any matter, that team automatically forfeits and their planet will be immediately destroyed.
- Commercial Break Cliffhanger: The show quickly goes to the second break right before Meldar reveals the name of the Earth contestant voted off. Doubles with Ad-Break Double-Take as he says the same line after the show comes back.
- Conscience Makes You Go Back: After Team Earth has won, Jimmy and April share a tearful goodbye as they prepare to go home. But upon realizing he can't break his alliance with April and let the losing teams suffer their planets being destroyed, Jimmy reprograms their new AstroCar to fly back to the show.
- Dying to Wake Up: Cindy suggests they try breaking out of the dream by jumping into the Bottomless Pit that's supposed to keep them corralled there. It works.
- Embarrassing Slide: While Jimmy is showing the presentation of the space rock, the last slide shows Sheen snorkeling in the toilet of his bathroom.Sheen: AAAAAHHHHH!!!! CARL!!!!
- Extra-Long Episode: The third after "The Eggpire Strikes Back" and "Operation: Rescue Jet Fusion".
- Killer Rabbit: The white rabbit-like alien during the second challenge is adorable on the outside, but once a contestant comes close enough, it shows its ferocious side and attacks them.
- Luxury Prison Suite: After being voted off of Team Earth, Bolbi is sent to the Cell of Indignity for the rest of the game and can only be freed if his team wins the game. The Cell of Indignity turns out to be pretty calm and relaxing, with Bolbi being catered to by three beautiful alien women. He was still relieved to be released and reunited with his friends though.
- No One Gets Left Behind: Even though Team Earth ends up winning and going home safe, Jimmy refuses to break the promise he made to April and flies back to the show to save the other planets.
- Non-Standard Kiss: Inverted; April presents Jimmy with the "Gorlockan Seal of Trust", which is like a normal, human kiss, albeit she doesn't know what a kiss even is. Averted when she does it again later, saying "that was a kiss" after Jimmy asks if that was the aforementioned seal of trust.
- One-Word Vocabulary: The Needleheads can only say "Mibs".
- Only Known by Their Nickname: April's real name is a series of random noises ("Chee-AHHHHHHH-Doik"), but prefers this more generic name for her sake.
- Properly Paranoid: Everyone believes that Jimmy should just leave the space rock alone, given his past with aliens. It turns out they were right as the rock was just a contestant search for a twist game show that could get Earth destroyed.
- Shout-Out: During the fake victory for the gang after they fall for the fake shortcut in the Obstacle course challenge, Sheen shouts this out.Sheen: Take that, Alien slime! Can you smell what the Earth is cookin!
- Show Within a Show: Intergalactic Showdown, the game show Jimmy and the gang are competing on.
- Special Guest: Tim Allen as Meldar Prime, and Alyssa Milano as April the Gorlock.
- Team-Based Tournament: The plot of the episode involves teams from all over the universe competing to not get their planet blown up. Team Earth initially struggles because Jimmy insists on working alone, and only starts winning when Jimmy starts working with the others.
- Too Dumb to Live: When Team Earth needs to vote off one of their members for being in last place, Bolbi ends up voting himself off because he thought that winning the vote was a good thing. Though it is zig-zagged since as a result he was sent to the Cell of Indignity where he was catered to by three beautiful alien women until the end of the game.
- Your Head Asplode: Happens to the Needlehead who eats the banana cream pie during the third challenge.
