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Inside Michael Bolton's Hilarious, Ridiculous Valentine's Day Special

We talk to Bolton and comedy team Akiva Schaffer and Scott Aukerman about getting cucked, losing your virginity, and trying to get Bill Clinton to play the saxophone.

Variety specials have long been a staple in the world of television, even in recent years (make sure to hunt down Lady Gaga's excellent 2013 special, Lady Gaga and the Muppets Holiday Spectacular, if you're looking for proof). Even the world of streaming TV has experimented with the genre: In 2015, Netflix released the Sofia Coppola–directed Bill Murray holiday special A Very Murray Christmas, and this year, the streaming giant dove head first into Valentine's Day with Michael Bolton's Big, Sexy Valentine's Day Special.

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Whereas A Very Murray Christmas played it straight, Michael Bolton's Big, Sexy Valentine's Day Special… doesn't. (The "sexy" in the title should be enough indication of this.) Conceived by Scott Aukerman (Comedy Bang Bang, Mr. Show with Bob and David) and the Lonely Island's Akiva Schaffer (Popstar: Never Stop Never Stopping, Hot Rod), the hour-long gonzo bonanza combines traditional hallmarks of the variety special genre—loads of celebrity guests such as sax master Kenny G and comedians like Fred Armisen and Sarah Silverman, and plenty of musical numbers—while adding tons of bizarro comedic gags ranging from VR cuckolding simulations, to filthy faux-Sonny and Cher duets, to the most ridiculous Mission Impossible: Rogue Nation homage that you'll ever see. Santa Claus plays a role in all this, too, because why not?

The special is a perfect melding of the comedic sensibilities of Aukerman (arch, surreal, and with a heavy dose of meta) and Schaffer (profane, silly, and just gross enough without going overboard)—and it actually works as a straightforward variety special, too, with Bolton's impressive pipes acting as a warm blanket to swaddle the special's over-the-top hilarity. I spoke to Aukerman, Bolton, and Schaffer about how they put the special together, the race to use "cuck" in a sketch before Saturday Night Live, and what music they lost their virginity to.

VICE: I feel like Comedy Bang Bang and the Lonely Island have very specific and distinct comedic voices—but both of them are represented in this special.
Scott Aukerman: I was just coming off Comedy Bang Bang—an in-studio, five-camera fake talk show—so I knew the exact angles to shoot this. And Akiva has a lot of experience doing shorts and major Hollywood movies.

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Akiva Schaffer: We were both winging everything. When one of us was a little tired, the other one would say, "OK, I'm taking this seat."

Aukerman: That's really the reason to do something together—you're there 16 hours a day, and it can get so tiring. We'd take over for one another and be like, "OK! My turn."

Michael Bolton: I never witnessed either one of them being tired—

Schaffer: But we've worked together in the past, too. Sorry to interrupt you, Michael.

Bolton No, that's alright. It's what I'm here for.

Schaffer: When [Andy Samberg] did [the MTV Movie Awards], Scott was the head writer. When Andy hosted the Emmys, Scott was the head writer, too. The idea came up for this in September of last year, so I knew if this was going to happen, it had to happen quick and I would need help with it. I got lucky that Scott liked the idea and wanted to do it.

Michael, you're really funny in this special.
Bolton: I am?

You are! You've done funny things before, but there's a difference between doing funny things and being funny. Were you worried about pulling off the latter when going into filming?
I was worried that I was going to be doing funny things that weren't funny. [Laughs] No, I wasn't worried. I learned so much from making the Lonely Island's "Jack Sparrow," because the guys are so hands-on in producing everything. They hear details like mad musicians—I love that, and I respect their work ethic, so I had confidence that whatever we did, it'd be covered musically. We used some of the songs from my upcoming album Songs of Cinema, letting some of the seriousness of it come across while having a lot of fun with it at the same time.

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Making "Jack Sparrow" taught me how to step out of my comfort zone, and the right directors and the right input brings the funny to these scenes. It's a big deal—when somebody says just try this, and the brakes aren't on.

Aukerman: It's about protection, too, because we don't want to put out a product where Michael's embarrassed. We have to make sure that the finished product is A+—and with that comes the ability to try anything on set, which Michael was great about. We'd throw stuff at him, and he'd just go, "OK!" That's so much better than having a star who thinks they know why they're funny, or what they're doing to be funny. I'm talking about Zach Galifianakis right now. He's not going to read this, though.

Michael, you were also featured in the "Incredible Thoughts" sequence from the end of Popstar: Never Stop Never Stopping. Every time you do something comedic, do you notice an uptick in interest when it comes to that side of your persona?
Bolton: The industry had definitely been responding. "This was so great, we've got to get you to do something like that. Would you consider this, this, and this?" And I reply, "Well, it depends on what Akiva and Scott say, you know?"

Schaffer: We have an ironclad contract.

Aukerman: It's basically a comedy contract—he has to run scripts by us, and if it's not funny, we allow him to do it.

Schaffer: We're happy to have him embarrass himself if he's not working with us. If he does something great, that's going to make us very mad.

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Did you guys grow up watching any variety shows?
Aukerman: I watched them religiously as a kid. There was nothing better than watching a variety special. It seemed like show business to me, and as a kid who found show business fascinating, that whole world was so cool. We went back and watched a few of them for this. I was watching The Brady Bunch Variety Hour. There was a specific applause sound that they used that I was fascinated by—tinny, poorly, and shittily recorded.

Schaffer: We tried to make this feel like a network TV variety special that goes completely haywire. We had a lot of takes where Michael would use a bad word, but he only curses twice in the whole special. He says "shit" once and "fuck" once, right?

Aukerman: He says "fuck" again after the credits, too.

Schaffer: We were tempted to just have him curse all over this, because every time he did curse it was always funny. But his character is really just trying to make a normal network special. Then things start unraveling.

Bolton: And then [Sarah Silverman] shows up, and nothing we say is nasty anymore. She's pushing the envelope.

Schaffer: She just wants to see your butt.

The segment where Chris Parnell talks about being "cucked" stood out to me. That word has entered the lexicon now.
Aukerman: We were excited that we were going to be one of the first sketch comedy shows to use the word "cuck."

Bolton: We beat everyone to the punch.

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Schaffer: Every week we'd watch Saturday Night Love like, "Please don't say cucked."

Aukerman: That was like the taint sketch in Mr. Show. No one had ever done a sketch about the taint, and I was super stoked that we were the first—then SNL did one, like, three years later.

Bolton: I'm working with pioneers here.

Were there any celebrities you guys tried to get to appear on this that you couldn't get?
I called Meryl Streep and she said she was busy. Nah, that's a complete bullshit lie.

Aukerman: Michael, we were really hoping that you were going to call your friend Bill Clinton to play the saxophone.

Bolton: That would have been awesome.

Schaffer: But we were shooting during election week. Any other week, he would've been there.

What's the song that was playing when all of you lost your virginity?
Aukerman: I don't think I was listening to anything because I barely had enough sense to turn the lights off—I was just like, "Sex! I want to see everything!" So I wanted to hear everything, too. But I do associate two records with sex, because it's what we were listening to a lot at the time, which is George Michael's Faith and Terence Trent D'Arby's Introducing the Hardline. Those are the two records I associate with that wonderful person who granted me the greatest gift a woman can give.

Bolton: She was your fourth grade teacher. Aukerman: Well, that was the unfortunate part.

Schaffer: That all came out in the news and has been dealt with, so we don't need to get into that now. You guys know mine—it was "Bird Is the Word." I had a CD changer at the time. Put it in. Repeat. Track 3. Boom. It's over.

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Aukerman: Why did you have a CD changer?

Schaffer: That's just a backdoor brag to let you know that I could've played five different albums of music.

Aukerman: That's just a detail we didn't need. We don't need to know that for the story.

Schaffer: I'm letting you know I chose one track on repeat when I had five albums worth at my disposal. The next one could've came on. Maybe it would've been Abbey Road.

Aukerman: Maybe it's just me, by the way, but I think the Beatles changed popular music forever.

Schaffer: That's really insightful.

Bolton: I didn't have a CD. When I put the cassette in…

Aukerman: You're pretending it was a cassette.

Schaffer: It was an 8-Trak.

Bolton: I just realized, Scott, you were calling [my dick] a cassette.

Schaffer: This is his sex thing. He called it a cassette. That's fucking sick.

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