Things got somewhat weird in the fifth and final Dirty Harry movie, The Dead Pool, which featured, among other things, an over the top segment where a pre-famous Jim Carrey lip-syncs to “Welcome to the Jungle” by Guns N Roses for a music video/slasher movie directed by Liam Neeson.
Although not quite as memorable as the music from the first movie, Bob Seger’s “Shakedown” from Beverly Hills Cop II is still a fun song that debuted at #1 on the Billboard charts and was nominated for a “Best Original Song” Oscar.
The second single released from The Simpsons Sing the Blues album, “Deep, Deep Trouble” was co-written by Matt Groening and DJ Jazzy Jeff and features Nancy Cartwright rapping as Bart about a series of events that landed him the title predicament.
The undisputed breakout star of the TGIF hit Dinosaurs, Baby Sinclair got his own song and music video alongside the slew of other merchandise featuring his face, “I’m the Baby, Gotta Love Me”, which aired during an episode in the show’s third season.
Recently winning the Oscar for Best Original Song, (I’m Gonna) Love Me Again was written by Elton John for the biopic about his life, Rocketman, and he performed it with his younger doppleganger, Taron Egerton.
Amongst all the bizarre aspects of 1991’s Nothing But Trouble, one of the strangest might be the appearance of Digital Underground as themselves, who charm their way out of punishment from the evil (and disgusting) Judge Valkenheiser by performing “Same Song” for him in court.