An iconic, Grammy Award-winning singer/songwriter who has sold over 75 million records and recorded eight top 10 albums, it would seem that there is little Michael Bolton hasn’t done.

Reaching the zenith of the music industry, recording alongside the likes of Celine Dion, opera powerhouse Luciano Pavarotti and mentor Ray Charles, Bolton has felt a little boxed in by the success he has achieved as a musician, only recently given the opportunity to explore another deep-seated passion—comedy.

Breaking out of the box, Bolton has, in recent years, explored this passion with Lonely Island collaborations, pit stops on popular sitcoms, including Two and a Half Men and Fresh Off the Boat, and a particularly fruitful meeting of the minds with Andy Signore on the massively popular YouTube series, Honest Trailersfrom DEFY Media’s ScreenJunkies—which fuses the two creative loves of Bolton’s life, satirizing the most popular movies of today, and of all time.

Speaking with Deadline, Bolton and Signore—SVP of Content at DEFY Media, and ScreenJunkies’ Head of Creative—discuss the roots of their ongoing collaboration, their comedic benchmarks and their Emmy-nominated take on Willy Wonka & the Chocolate Factory.

Screen Junkies

Andy, could you give a sense of how Honest Trailers came to be and what inspired it?

Andy Signore: It was done as a one-off in the beginning, when Star Wars: Episode I came out. They rereleased it in 3D and had put out all these trailers that were so excited for the movie, and I watched it going, “We know the movie’s not that good. How dare you try and trick us to tell us it’s something it’s not? We’ve seen it already.”

This idea then came out: I was like, “I’d love to see an honest voice—like, a trailer guy—do the honest take of a trailer, and do it all in the deep, big voice.” So we did it. We made the first installment—it was pretty good, a pretty big hit, and we decided to follow up with Twilight, Transformers, Titanic.

Each one became bigger and bigger, so we quickly stumbled upon a format that I think resonated with the audience. It’s taken us through almost five years now, two Emmy nominations, and celebrities like Ryan Reynolds and Michael Bolton. It’s beyond my wildest expectations.

How did Michael come into the fold? What excited you about him as a collaborator?

Signore: I was always a fan of Michael, and I had reached out to his reps forever to try and figure out a way we could work together. We had been in talks, and he had been helping from afar. We were looking for the right song to do an “honest medley” for, and “Willy Wonka” came together. This was the one that I was hoping he would be into. He was, and he’s like, “Let’s sing this.”

That’s when he got to be more ingrained in an actual trailer. We were very lucky to have his talent there.

Screen Junkies

Michael, what was the draw for you?

Bolton: I’ve worked my ass off since I was a teenager, had a chance to be in the music business, and worked through a lot of years where I think I was always taking everything so seriously. It took me 18 years before I had my first hit, after I signed with Epic [Records] when I was 16. People would never really see the funny side of me, or what I loved, which is comedy.

The Lonely Island guys brought me “Jack Sparrow,” and I did that—it was so much fun, and we took time to develop it. It gave me permission to be the kid I was ever since I can remember, who got to know the principal very well at every school that would have me, and basically have fun.

What Andy and Honest Trailers bring is a lot of laughter and high sonic value, musically. It’s something I like to be able to do.

I’ve sung with Pavarotti, I learned classical. My mentors are Ray Charles and Stevie Wonder, but I love everything in between classical and R&B. They give me a certain amount of freedom, and offer me permission to basically be myself, and bring something that’s legitimate to something that is very funny, very smart, with extremely high quality footage in front of you and high quality music.

Andy didn’t have to twist my arm. I just found out that when he was a kid, he did a video of “Steel Bars”, a song I wrote with Bob Dylan. I don’t know how many people got to write with Bob Dylan, but the entire time I was working with Bob, I was looking at him and he was talking to me about taking the car up in the [takes on Bob Dylan’s voice] “four-wheel drive.” I was looking at him and thinking, “Oh my God, this is Bob Dylan. I’m sitting with him.” So we’ve been having conversations like that.

I’m excited about the Emmy nomination, to be able to talk with Andy about the fact that it’s great to have the industry support you. But your career is going to be [defined] by doing great work. If you win, that’s awesome. You’ll find a place in your home for that trophy. It’s exciting and an honor when the industry is voting for you.

Screen Junkies

You’ve done a lot of comedic work in television of late, including a Netflix Valentine’s Day Special. For both of you, who are the people you admire in comedy? What are the touchstones?

Bolton: Because you mentioned Big Sexy Valentine’s Day Special: I’m a Lonely Island fan, and the people who showed up for us—from Andy Samberg and Jorma [Taccone] and Akiva [Schaffer]—everybody they asked to show up for the special showed up.

Last night, I filmed something with Randall Park, and I was thinking, “How did this all happen?” I got a phone call about a “Jack Sparrow” video four or five years ago—it feels like it was yesterday—and then all these people show up and they become family. Maya Rudolph, Fred Armisen; Sarah Silverman came in. She wrote some disgusting lyrics and it was hysterical, and they were so gracious to work with.

That’s kind of the new world for me. What Andy offers by coming to me and saying, “Can we work on this together? You interested in this?”—it taps every dimension that I enjoy. I loved film since I was born, and love comedy. The fact that I might be able to sing something R&B, something classical, and something that works for the project, but is just one facet of singing for me, gives me the means to express myself and have a freaking great time, and laugh our asses off at the whole concept of it.

The quality is high, sonically and visually. We get this insane footage—we couldn’t do this in the video world. It’d cost us a fortune if every one of our songs had that level of footage. But it’s also going to these iconic moments. For some reason, this is the time in my life and my career where I keep being given positions. In this case, with Andy and his team, I’m being given options for different projects. So I love the collaboration.

Signore: Musically, Michael was a huge inspiration for me as a kid. He’s not lying: I did a music video for “Steel Bars”—I think I was seven or eight—with my brother and sister. I had very eclectic [taste in] music. I loved everything.

But the true idol for me was “Weird Al” Yankovic. He was a huge inspiration for me, in comedy, and as a lyricist and musician. He’s so talented. I was really raised on “Weird Al” and The Simpsons, for my comedy chops.

We’ve been doing this Emmy talk, and it’s such an honor to have this Emmy [nomination], but as I’ve said, the win for me, right now, is being able to have someone like Michael, who I look up to tremendously, who is such a legend, and has done so many things that I look up to, and many do. To have someone of that stature like to work with us, and be happy to do it, and partner with us on the series and come back to do more, that’s the win in our eyes.

Doing the work—trying to win awards is not our goal. It’s icing on the cake, and it’s definitely fun, but being able to work with someone like this, and have fun doing it, that’s the true win.

Bolton: No pressure on me. [laughs]

Signore: I do want to put it out there for Academy voters: Let’s get Michael an EGOT. Come on, he’s almost there.

What was involved in crafting lyrics for your “Willy Wonka” video and recording the track?

Signore: A friend of mine, Matt Citron, does our music and gets feedback from Michael. Matt is our composer who does a lot of the heavy lifting for us, musically. On “Willy Wonka” specifically, Matt and I had been talking with Michael through previous episodes, but we hadn’t really got to record with him.

The “Willy Wonka” experience was very surreal for Matt and I. We had written this very silly song, and I knew what Michael was going to bring to us, so I was very excited. To be able to get there and be so collaborative, and have Michael take the wheel, musically and vocally, to have Michael Bolton sing the Oompa Loompa song was really a bucket list item I didn’t know I had to have checked, and I’m so glad I did.

He was so collaborative in there. What was it like for you when we were throwing the Oompa Loompa and Creepy Man at you, on the day?

Bolton: The Creepy Man was creepy. I’ve learned that the stuff that can creep you out can be funny stuff. The torment and terror reads through the screen.

Signore: That candy man is very creepy. And mean! All those people are just eating all that candy in front of Charlie. [laughs]

How many takes did you go through to get the track down?

Bolton: I can’t remember how many we took.

Signore: Look, Michael knows when it’s ready. I hear it, and I go: “Wow!” Michael hears it, and he knows he can make it better—and sure enough, Take 3 is the winner. We have a knowledge of our comedy writing and what we’re doing there, but I knew to defer to him on that, musically, and he did not disappoint us. He knew which take, he knew his voice; he knew when he had it right.

He also knew that that song wasn’t really written for him, and he was like, “Next time, let’s try and do something more fun,” as we progress and do more things vocally, so he can riff, because he has such an amazing range.

The takeaway for me was in figuring out next time, how do we get something we can play even bigger? One of my other fellow writers wasn’t as familiar with Michael. He knew of Michael, but he wasn’t as impressed when we scored Michael.

Then, when he heard the take, he was like “Oh my God, I get it. This is amazing, you were right. Now I get why you were pushing me to get excited for this.” He just has that talent, that edge, that most singers don’t. And still has it! I want to give him the props: his Songs of Cinema is fantastic.

What do you hope to do together in future collaborations?

Signore: We’re working together right now on a very lofty, epic project, and Michael has been very gracious to try and fit it in. I’m excited about trying something new, challenging ourselves with something different. But I’m glad he’s still taking our calls—I’m glad he’s still a fan of the show. He’s a busy guy.

To take a look at Michael Bolton’s Emmy-nominated Honest Trailers endeavor—teasing out the bizarre world of Willy Wonka—click here. 

And in anticipation of the upcoming Emmys ceremony, Michael Bolton has teamed up once again with the Honest Trailers team for a hilarious take on “Honest Retro TV Themes.” To view the musical montage—featuring performances from Bolton and friends, including Natasha Bedingfield, Brian McKnight and Paula Cole—just hit the link.