- Eating popcorn in the Thriller video. The blissful smile makes it ten times better. (But of course many of you know that thanks to Memetic Mutation.)
- "Smooth Criminal" from Bad, especially in the Moonwalker cut is a mix of Coolness and Funniness.
- The first entertainer getting thrown to the lions in the music video of Remember The Time from Dangerous.
- The father being blasted to Africa by Macaulay Culkin's radio sound in the music video of Black or White from Dangerous. Plus, said father is played by George Wendt.
- In the music video for Jam, after showing Michael Jordan botching a dunk, it then cuts to Jackson casually tossing a basketball over his shoulder and kicking it—with his back to the hoop, mind you—and it goes in nothing-but-net. Jackson is thrilled; Jordan just kind of looks at him in disbelief.
- Also, both during and after the video, Jackson trying to teach Jordan how to dance and moonwalk. It doesn't go so well.
- The cross eyed faces he makes in Michael Jackson's Ghosts. Even funnier in the B-Rolls.
- Kenny Ortega giving some directions to an assistant as they're testing a cherry picker for the "Beat It" number and nonchalantly scolding Michael for not holding on to the railing in This Is It.
- The discussion between the male backup dancers and the female choreographer on how to best perform the iconic crotch grab move. They can't decide if the guys should actually grab themselves or to just mime it, with the choreographer commenting the latter looks better but also points out that she has nothing to grab to really notice a difference.
- The ending of the "Speed Demon" video, where he's given a ticket for being in a "No Michael Jackson-ing Zone." Especially the way the cop asks for his autograph as both literal and figurative.
- This moment is both funny and heartwarming: Michael had a song called Dirty Diana which was about a groupie called Diana doing shameless things with band members to get famous. A while after the song's release, a concert was to be attended by the Royal Family including Princess Diana. Out of fear that the Princess would be offended, he took the song out of the set list for that show. However, when Diana found out, she told him that it was her favorite song and unfortunately it was too close to showtime to put the song back in.
- In his tour of Neverland Ranch, Macauley Culkin pushes him off the diving board while he's doing the Billie Jean dance. In another video, Michael is pushed into the pool by some kids, all the while shouting, "I'm a nice person! I just took a shower and I washed my hair thoroughly!"
Funny / Michael Jackson