- An hour before a performance in 2004, Al got a call from his wife telling him that his parents had both died from carbon monoxide poisoning. What did he do? He went and performed, saying to his fans, "since my music had helped many of my fans through tough times, maybe it would work for me as well" and that it would "at least...give me a break from sobbing all the time." He would go on to complete that entire tour with no hitches.
- He did, however, cancel a meet-and-greet afterwards to recuperate (to which ZERO people blamed him and even ENCOURAGED him), and took some time off after the tour to be with his family.
- So Coolio wasn't happy about "Amish Paradise". Well, recently, after what seemed like a longtime rivalry between the two, you need worry no more.
- When asked about the whole incident afterward, Coolio said that he "really thought it out. I was like, 'Wait a minute.' I was like, 'Coolio, who the fk do you think you are? He did Michael Jackson. Michael Jackson didn't get mad,'" Coolio also has mentioned that complaining about Amish Paradise was "one of the dumbest things I did in my career."
- When Weird Al's parody, "Perform This Way" (a parody of Lady Gaga's "Born This Way"), was (initially) rejected by Gaga's manager (Lady Gaga herself would later give Al the OK to release the parody), he encouraged donations to the Human Rights Campaign as an act of "good karma," because of the original song's human rights message.
- A few years later, when several famous musicians cut North Carolina out of their tours in protest of the state's controversial transphobic bathroom law, Al announced that he would keep the state on his schedule so as not to punish his fans, but compromised by donating whatever money he would make from the show to the Human Rights Campaign.
- Al Yankovic follows many people on Twitter, but only one list: "People I Am Sleeping With", consisting of his wife Suzanne.
- The last shot of the "Al in the Studio" documentary on "Straight Outta Lynwood", with Al's daughter Nina watching him work.
- Unlike most musical parodists, Al famously goes out of his way to ask permission from the original artists, even though he's legally allowed to do it with or without their approval, simply because he wants them to be in on the joke and avoid stepping on any toes if the song is too personal to them and has almost never made cheap shots at one. Aside from his mentions of being annoyed with Prince or Coolio, the only two songs where he mocks the quality of the artist are "It's Still Billy Joel to Me" (Billy Joel) and "Achy Breaky Song" (Billy Ray Cyrus). Al seems to regard the former as an Old Shame, as it's never been released, and the latter was so upsetting that Al donated money to the charity of Billy Ray's choice. He even goes the extra extra mile to thank them all individually in the liner notes of his albums.
- When Weird Al got married, there was a rainbow behind him and his wife for some of the pictures.
- Mandatory Fun is Al's first #1 album. And Al was just over the moon that morning.
- Whenever Al gets letters from fans writing about how his music helped them through bouts of depression or kept them from committing suicide, or even how "One More Minute" helped them get over heartbreaks, it really makes his day. He once said that he never dreamed his music would have such a positive influence on people.
- The day Doors keyboardist Ray Manzarek passed away, Al posted a video of him recording his keyboard parts for Al's Doors parody "Craigslist," along with a description of how it was one of the seminal points of his musical career.
- Al, Jodi DiPiazza and the Actionplay Chorus at performing "Yoda" on Night of Too Many Stars (a benefit for Autism). Doubles as a Moment of Awesome for Jodi and the chorus.
- Al brings his daughter Nina (dressed as a Jawa) onstage during this performance of The Saga Begins.
- The ''Fireflies'' snippit in "Polka Face" does a great job retaining the sweetness that the original version had.
- Following a career's worth of pot-shots at Prince for refusing to let him parody any of his songs, Al posted this the day The Purple One died, later saying that he'd continue to respect his wishes and not release any future parodies of his songs.
- Heck, just meeting the guy can be this! Fans lucky enough to have met him note just how appreciate he is of having them, not to mention just how gentile and polite he can be.
- This troper and her husband met him at a convention two months after Hurricane Matthew. The convention was originally scheduled for the weekend of the hurricane, and Al was one of the only guests who adjusted his schedule to be there.
- His absolutely adorable interview with child YouTuber Lindalee Rose for Milo Murphy's Law, especially the ending when he's clearly playing with her to make her laugh. It's clear that all those years raising a daughter has had an effect on him.
- His first children's book, When I Grow Up, is not only incredibly charming, but has the wonderful message that it's okay to want to have more than one career in your lifetime, no matter how old you are.
- Dav Pilkey was apparently kept in the dark that Weird Al would be singing the theme song for the Captain Underpants Movie (fitting not only for an artist as silly as Al, but also because one of George and Harold's pranks in the first book involved rigging their school's PA system to play Weird Al for 6 hours straight), and was absolutely delighted when the trailer dropped that contained the song.
- Unlike nearly everyone else who's received a star on the Hollywood Walk of Fame, who had the application fee(s) paid by a studio, agent or similar, Al's fans organized themselves and paid the fee twelve times (the final fee was $40,000!) before the application was successful.
Heartwarming / "Weird Al" Yankovic