The number 27 occurs frequently in his works.
Why 27?
I’m guessing: Because it’s a strangely specific number being used in situations where an approximate number would logically be expected. He has no reason to specify 27, and having no reason is exactly the reason he does it.
“It’s Still Billy Joel to Me”, a parody of Billy Joel’s “It’s Still Rock and Roll to Me”, was originally planned for Al’s debut album. According to wiki,
Even though it was never officially released, it somehow got released via other channels. Here it is.
Not everything was a parody. Here’s a straight cover:
77 Covers by Al and his band
(Am I the only one who thinks the capitalization in the thread title makes Weird al-Yankovic look like an Arab?)
… which would mean Weird was his given name, and his last name meant “the Yankovic”. Works for me. 
There are interesting similarities between the backgrounds of Tom Lehrer and Weird Al Yankovic. Both learned to play an instrument as a child. Both entered college early. Both got degrees in technical fields unrelated to music. Both are satirical singer/songwriters.
At least when comparing only that of their material that’s become famous, Lehrer’s satirical stuff was much more “edgy” and tended to take on grittier or more serious topics (We Will All Go Together When We Go, National Brotherhood Week, even the more comedy-oriented Poisoning Pigeons in the Park).
To clarify, Weird Al played Wreck-Gar in the Transformers Animated TV Show, which is a different storyline than Transformers: The Movie from the 80s. I would say different continuity, but I have no idea about continuity in regards to Transformers:
I did not realize this but he was Darkseid as well:
He was also the voice of Dollmaker in the DC original animated movie Batman vs Robin, which IMO just served to make the character even more disturbing.
Also, Weird Al will be getting his star on the Walk of Fame
Fantastic!
And he really needs to be in the R&R HOF.
There’s a youtube video of Al making a surprise appearance at a Weezer concert, joining in on their cover of Africa with his accordion. Watch carefully, as he leaves the stage the keyboard player raises his hand for a high five, and Al does a fist-bump instead.
Al’s degree is in Architecture. If memory serves, I think he had intended to go into music, but got the degree to appease his parents, because they were worried that career would be too unstable. This way, he always had something to fall back on.
His degree is from my alma mater, Cal Poly, San Luis Obispo. I had a couple of friends who were there when he was. He used to work at KCPR, the campus radio station, and his demo tape that he sent to Dr. Demento was recorded in the bathroom at the Graphic Arts building.
Al currently does the voice of the title character in the Disney animated series “Milo Murphy’s Law” (which is great, by the way) and there are some really good songs in the episodes. I don’t think he wrote them, but he performs some of them.
Interestingly, one of Al’s “competitors” in I Lost on Jeopardy was an architect, although Al holds a bachelor’s degree, unlike the one in the song, who was a Ph. D.
Yes, Weird Al Yankovic’s degree is in architecture. He entered college at 16. He learned to play the accordion as a child. Tom Lehrer’s degree is in mathematics. He entered college at 15. He learned to play the piano as a child. Those three things (and the fact that they do satirical songwriting/singing) was all I’m claiming are similar.
Listen to this episode of Behind the Music. It’s at 8:30. Weird Al says that when he was about to graduate from high school, a guidance counselor said to him, “You’re good at math. You’re also interested in artistic stuff. You should become an architect.” Weird Al said that he was thinking of becoming a cartoonist. (Um, I think that’s what he says.) The counselor said, “You’re never make any money at that.” So he majored in architecture: