Weird Al has adapted to the Internet better than any other artist from the 80's. His Chamillionaire parody "White and Nerdy" has over 50 million views on YouTube, and is currently one of the site's most popular videos of all-time. The song was his career peak, going all the way to#9 on the Billboard Hot 100 (his previous best – "Eat It" at #12 in1984). Since then he's explored digital distribution which, for the first time in his three decade career, has allowed him to parody current events and songs that are popular right now. Really, it's hard to believe Weird Al survived at all – much less thrived – before iTunes and YouTube. He recently released The Essential Weird Al collects 38 of Al's best songs into two discs.

CollegeHumor: How did you decide which were the greatest hits from your distinguished career?

Weird Al: It was tough. I've got twelve studio albums of material and I did have to leave off a lot of stuff that some fans think should have been on the essentials collection. There's some historically important ones missing. "My Bologna," isn't even on there, which was my first pseudo-hit. Even though My Bologna was historically important, it wasn't so brilliant I would consider it among my best work. So I had to weigh fan favorites with what I thought were songs that actually merited being on a best-of compilation.

CH: So you hand picked the songs yourself?

WA: I did, yeah.

CH: When you were going through your earlier albums, did you rediscover any material that you'd forgotten about?

WA: I don't think I'd actually literally forgotten about any of it but it was kinda nice to listen to some of the old tracks again that I hadn't heard in a while. It also was an opportunity to clean up a couple things. This new collection is completely remastered. It's not remixed, but we cleaned it up. I won't mention where exactly because I don't want people to obsess over it the way I did, but there were a couple songs that had a few little pops and ticks and just little things that probably most people have never heard before in their life but they'd been bugging me for 25 years.

CH: When are you going to drop the hammer on Lady Gaga?

WA: Well, nothing is guaranteed but she's certainly a prime candidate and somebody that I'm thinking about. Whether she makes the cut or not, we'll find when the next album comes out.

CH: You are by far the number one selling comedy musician of all time. Do you even know who number two is?

WA: Uh, I don't.

CH: Why do you think there are no other Weird Als out there?

WA: I don't know, I guess the zeitgeist only had room for one and I got it. I just started at the right time and had a few lucky breaks and worked hard at it and surrounded myself with talented people and I've just been very lucky I guess.

CH: Do the usual rules of the music industry apply to Weird Al? You have such a unique position in that no one else is out there doing what you do.

WA: Yeah, I guess it's a little different for me. One of the nice parts about it is that I can shamelessly follow whatever trends occur in pop culture and I can't really be labeled as a sell-out because that's sort-of my job definition. That's what I'm supposed to be doing. I'm supposed to be a shameless leech, and I do it well.

CH: You recently topped a Rolling Stone poll of people who should be inducted into the Rock and Roll Hall of Fame. How did you react?

WA: Yeah, that's amazing. I've got the best fans in the world. I'm just extremely flattered and grateful that my fans care enough to put that out into the world. I don't think that that's going to influence the Rock Hall, I don't really think they have the sense of humor to acknowledge whatever contribution I may have made to pop culture, but the fact that fans care enough to start doing petitions and make the effort, that means more to me than anything else.

CH: Is there a typical kind of Weird Al fan?

WA: The joke is that all my fans are twelve-year-old boys which is not true, but I can kinda see where that myth comes from because that's probably my most energetic hardest-core fan. But all you have to do is go to one of my live shows and you'll see that the appeal is really multi-generational. It's everything from young kids to college age to grandparents, so it's a family show. It's something that I think has a pretty wide appeal, and the people that were into me in the 80s when I was first starting out seem to have hung in there and they're still fans to this day and they're bringing their kids along now. I've been told it's sort of a bonding experience for some families.

CH: This year is the 20th anniversary of UHF. Any reflections on the film?

WA: I'd like to go back and re-edit it and add a couple scenes and maybe take a few out. I re-edit the movie in my mind every night before I go to sleep.

CH: Do you do that with your other work? Do you wish you could change certain lyrics in a song, or is this specific to the movie?

WA: I think that every creative person that is a perfectionist is never completely happy with anything they've ever done. UHF was such a big undertaking and my manager and I, who wrote the movie together, we kinda didn't know what we were doing at the time. I feel like I could do it better now. I'm very grateful that there are so many hardcore fans of the movie that have memorized it, and obsessed over it, and it definitely has become a cult classic for a lot of people, but I always feel like I coulda done better, or I coulda done something that would have would have made it more popular when it came out.

CH: Now whenever you see it, it's always described as the cult hit.

WA: When it first came out it was a bonafied flop. People stayed away in droves and the critics pretty much massacred it, but it's built up a following through cable TV viewings, VHS, and DVD rentals, to the point that when it was released on DVD a few years ago it was a top ten best selling DVD. It becomes like the Rocky Horror Picture Show with people chanting along with their favorite lines on the screen. That first weekend that UHF came out I didn't know it was going to have such an afterlife

CH: Do you feel any vindication now that the movie's generally regarded as, you know, good?

WA: Oh absolutely. It means a great deal to me when I hear from people that really enjoy UHF because it was a [laughs] pretty traumatic when it first came out. The test audiences gave it high scores, and Orion pictures had gotten its best numbers since Robocop, and they had such high hopes for it and those hopes were just dashed opening weekend so it's taken me a couple decades to [laugh] feel good about the movie again.

Check out The Essential Weird Al on Amazon.