The creators and writers of Jeopardy! apparently love "I Lost on Jeopardy", as they've referenced it many times. (The song references the Art Fleming version from the 1960s and 1970s, of which the Alex Trebek version — which came out mere months after "I Lost on Jeopardy" — is a revival.)
Michael Jackson was a big fan and enjoyed the parodies of his work. He even lent the set for his "Bad" music video for Al to use for his parody "Fat".
Chamillionaire told the Houston Chronicle: "It's one thing to go platinum. Where do you go from there? Then Weird Al calls."
Averted with Red Hot Chili Peppers ("disapproval of god?"). While they did give Al permission to do "Bedrock Anthem," and are fans of Al's work, RHCP bassist Flea later stated that the band members weren't impressed with the parody.
Development Hell: A minor example with Off The Deep End: Al had the problems with Michael Jackson and Paul McCartney detailed below (though they were very respectful about it) and after his hiatus at the time wanted to come back strong with a parody of a major hit. Cue Smells Like Teen Spirit becoming huge and thus Smells Like Nirvana was born and the album got on the release track.
Essentially the cause of Coolio's beef with Weird Al. Al usually got permission directly from celebrities for his parodies (even though he does not legally have to) but occasionally relied on the studio heads to do that for him. His producer got permission from Coolio's producer but not Coolio. After that incident, Al goes directly to the artist for permission.
Used in the more traditional sense with the song "You're Pitiful" which was supposed to be a parody of James Blunt's "You're Beautiful". James said yes, but the higher-ups said no, and the song was only released on Al's website for free.
Happened with his parody of Lady Gaga's "Born This Way." Al thought Gaga had not given him permission to put his parody on his new record, when what actually happened was her manager hadn't given Gaga the song to listen to in the first place, just assuming she would hate it. Once Gaga finally heard the song, she loved it.
Not to mention the hoops that Gaga's manager made Al jump through. Normally, Al doesn't even write a parody until he's gotten permission, but Gaga's manager insisted that she needed to hear it first, so he wrote the lyrics and sent them. Her manager's reply? That she needed to actually HEAR the song. Al, obviously thought it was weird since it was just going to be his lyrics with her music, but, as he wanted to use the song regardless of whatever hoops he had to jump, he went ahead and recorded it. When he got the rejection, he wasn't happy. As it turns out, however, Gaga's manager had never even sent her the lyrics, let alone the song itself, so she actually had no idea that the song existed, let alone was rejected.
Al's record label insisted that he include a Cyndi Lauper parody on Dare To Be Stupid, resulting in "Girls Just Wanna Have Lunch", a parody which he later admitted was "forced". Another instance on this album is his cover of the theme to "George of the Jungle"; apparently the label suggested that he do a cover song.
One album later, they wanted a Christmas song. The result, naturally, was "Christmas At Ground Zero".
Hey, It's That Voice!: Tom Kenny appears in a couple of Al's songs, including one of the breaks in "I Can't Watch This" ("Our prices are iiiin-SAAAANE!") and the bridge of "TMZ" ("Everything celebrities do is fascinating!").
Money, Dear Boy: His stated reason for recording "Eat It" and "Like a Surgeon." The latter was his biggest chart-topper until "White and Nerdy."
One of Us: The White And Nerdy music video alone proves this as only a real nerd would have known some of these things. Knowing about The Star Wars Holiday Special and why you would need to bootleg it is some serious nerd cred.
His bandmates, too. "Bermuda" Schwartz, for example, helped maintain Al's original web page and participated in Al's Usenet fan group.
"Pancreas" includes a near-perfect recitation of Newton's Law of Universal Gravitation (it drops a "squared").
And then there's "All About the Pentiums", which came out earlier and is labeled as one of the earliest nerdcore songs ever.
He's a Brony, and even had a guest role on the show.
Which would be Hilarious in Hindsight for those who heard "Stop Forwarding That Crap to Me", in which one of the lyrics implies that he doesn't care about unicorns. Doubly funny when you consider that he actually tweeted a fanmade music video that joins Friendship is Magic and Polkarama - thereby making HIM the one "forwarding unicorns".
Throw It In: In the video for "You Don't Love Me Anymore," bassist Steve Jay chipped one of his teeth biting into a piece of ham (watch carefully — he noticeably winces as he does so). Since it fit with everything else, it was kept.
The picture falling off the wall at the beginning of the video for "Eat It" wasn't intended but fit the mood well enough that they used that take.
Paul McCartney, a fan of Al's work, vetoed Chicken Pot Pie since it was about eating meat, as McCartney is a vegetarian.
Similarly, Al wanted to do a parody of "Free as a Bird" as "Gee, I'm a Nerd", but it was turned down by Yoko Ono. He performed it live a few times, however.
While "Buckingham Blues" sounds like a typical blues song, the opening lines and insistent references to the prince and princess as Chuck and Diane make it clear that it was originally conceived as a parody of John Cougar Mellencamp's "Jack and Diane". Al later used a parody of that song in his Simpsons cameo.
"Snack All Night" (Black or White, rejected because Michael Jackson felt it undermined the anti-racism sentiment of the original).
Imagine if Prince OK'd any of Al's parody ideas!
Al got accordion lessons for his seventh birthday. However, he could've gone with guitar lessons instead. Imagine that...
Bassist Steve Jay almost got a chance to audition for Frank Zappa, but didn't quite make it. So then he answered a newspaper ad from some guy named Al...