Presented by GRAMMY.com, Living Legends is an editorial series that honors icons in music and celebrates their inimitable legacies and ongoing impact on culture. Ahead of his Sept. 3 show at the iconic Hollywood Bowl, Michael Bolton looks back on the trying times of his early career and how it led to blending his love of music and comedy.
Nearly 50 years into his career, Michael Bolton isn't worried about staying relevant — he's simply trying to have fun.
This year alone has seen Bolton perform incognito on "The Masked Singer," co-star alongside Awkwafina in "Nora From Queens," and cameo on the HBO Max sitcom "Clone High." And amid all of his screen time, Bolton reignited his love of songwriting with Spark of Light, his first album of original music in 14 years.
Whatever he's doing, Bolton's goal remains the same: never take a moment for granted. Perhaps that's because his legacy took 18 years to begin, or due to his humble Connecticut roots.
Despite being a two-time GRAMMY winner with more than 75 million albums sold worldwide, Bolton has never thought of himself as one of the greats — but he's always been happy to be considered as such. That humility has given him longevity, along with a comedic sensibility that proves he's never taken himself too seriously.
Bolton's humorous side was most famously displayed in 2011, when Bolton teamed up with comedy troupe the Lonely Island for "Jack Sparrow," a hilarious short that ironically saw him dress as Gump himself (and, of course, Jack Sparrow). Since then, Bolton's career has opened up to generations who he never imagined would know the likes of "How Am I Supposed To Live Without You" or "When A Man Loves A Woman."
Combining his loyal longtime fan base with the new, Bolton is still getting to play venues like the famed Hollywood Bowl at age 70 — and, of course, taking in every minute of it.
Just after getting back from a stretch of shows in Asia, Bolton caught up with GRAMMY.com about his resurgence as a comedic actor, his advice for struggling artists, and why he considers himself the industry's Forrest Gump.
You, sir, have had quite the ongoing impact on culture, I must say.
Are you talking about my long hair or my records? [Laughs.]
Well, both, but also you're still doing all of these different things, between "The Masked Singer" and "The Dating Game" and such. It's really cool to see the ways that you're staying active in today's pop culture, not just leaning on your legacy.
I guess that's what they mean when they say "staying relevant."
Yeah, I suppose. [Laughs.] But it always feels genuine for you. I think there's a difference between trying to stay relevant and doing a genuine thing.
Creative work is the thing that leads to legacy and allows you to continue momentum moving forward. And it gets you together with really great creative people like the Lonely Island guys.
I was starting to have a great career of hits, and I realized I love comedy. And I had this opportunity, working with the Lonely Island guys from "Saturday Night Live," that I could have fun, take shots at myself — and others — and keep it musical as well. I think we're over 250 million views on the "Jack Sparrow" video.
And I agree with you — you can't get there by chipping away and refining and digging into details. You have to do it naturally, because people can feel it when it's contrived. But they also can feel it when it's real.
That's why we're working with a lot of creative people who are making films as well as streaming TV. I've worked with a lot of young songwriters and producers on this newest record, Spark of Light, to get their input and get a fresh take on music today. At the same time, the young writers and producers are looking to me to get a classic take on music. Because they want their music to be part of a catalog that [lives on] 30, 40 years later. People know your music for all different reasons than just putting it on a record and promoting it.
There is a stage where you're thinking, Is this too much? But I learned that comedy and music create the gift that keeps on giving.
And that's exactly why people love the Lonely Island, right?
Yeah, yeah. And I never planned on that. I was a big fan of theirs, and I was a big fan of "Saturday Night Live," but I never thought I would carve out something like the "Jack Sparrow" video, which opened up a generation, or two generations, behind me who have become fans since then.
Did you feel like you saw a shift in your audience after that? You said that it opened up your music to new generations, but was that a tangible thing?
Yeah, I witnessed it. I felt it.
[The night it aired], I found a place to hide in the ["SNL"] building while everyone was watching it, because if they [didn't] like it, I [didn't] really want to go through that. And they loved it.
John Mayer was there that night — he's a friend of mine from Connecticut. And he said to me, "Tomorrow, you're gonna see something you've never seen before." And I said, "Well, tell me it's gonna be good." And he said, "No, no, they're gonna love this."
The next day, I came downstairs, and my daughter was at the kitchen table, reading the quotes that were coming in from people, their responses to the video. She looked at me and said, "Dad, you're not going to believe what's going on."
From that time on, younger people in the streets would recognize me — it would be about "Jack Sparrow" and about the comedy, when for many, many years before, it was always about long hair, the hits, my rock days. The people who love this video were eager to hear what I was doing next musically.
Was comedy something that you were passionate about before then? Or something that you wanted to bring into your career?
I've always loved it from a certain distance, because my primary focus was music since I can remember. I was probably around 11 or 12 years old when I picked up my first guitar. I was listening to a lot of blues, like the Paul Butterfield Blues Band. I fell in love with the blues and started playing electric guitar, and put together a band. I knew what I wanted to do, and it was make music.
But comedy was something I loved. I was constantly in trouble with the principal at my school, because I couldn't take the work seriously. When they found out that I was being signed to Columbia Records, to Epic Records, they stopped putting pressure on me to cut my hair. And the next thing we all knew, I was having a career in the business. But it took me 18 years to have my first hit.
So many people would have given up after waiting that long. What kept you going?
What kept me going was that love for it. I'm grateful that I was surrounded by women most of my younger life. And my mother was so supportive of me pursuing music [growing up], and [now] I have three daughters.
But if I knew how hard it was going to be, I'm not sure I would've made the trek. Because there was so much time when there were no paychecks coming. And you're in the music business in Connecticut, if it snows, your concert is closed. So the promoters will call and apologize, but when you hang up the phone, you realize you have to figure out how you're going to feed your kids at night. That's the most intense pressure and excruciating experience for the "starving artist" syndrome — the reality that you may not be able to provide for your family.
We were getting eviction notices and our landlord would beg me to make sure the next check didn't bounce. So I started writing songs for other artists, and I was able to put full focus on my next record, and the one after that, and the one after that in '83. It all came together.
I tell young people that, whenever somebody says, "I've been at this for 10 years already," I say, "It took me 18 for my first hit, so don't give up. But know that it can take that long. And when it does finally happens, it's an even greater success story."
What do you tell people when they ask you about how to have longevity as an artist, especially since you did have such a long road to success?
My first instinct is compassion for anybody who's been at it this long… Having success once is not enough. I've seen people win GRAMMYs, and the next year, they disappeared from the map.
It took me longer to appreciate the success that I was having, because there was a part of me that was so protective of my own heart. I didn't want to get too excited. I find that it's not as big of a success as everyone was claiming it was. I didn't know how to celebrate success until I was sure [it was a success].
When you finally start to have success, and you've been hungry for so many years, you move into a different gear, to a different mode, wanting to ensure the continuation of success for your catalog. You realize that you can't take anything for granted, so you learn how to promote your records better. You learn how to partner, be a better teammate for the record label.
If you do your job right in the studio, making your record, it's going to do most of the heavy lifting for you. It's going to create word of mouth, you're gonna have core fans coming out and supporting you. But you can never take it for granted.
You started out as a songwriter and had a lot of success doing that. Is there a song that you gave away that you wish you would have recorded?
I don't think so. I've passed on some songs that were played for me, that were ballads that felt a lot like what I've done in my career already. And it felt like they're not a career changer. I think I could've had fun singing it, but it's not a real test record — like a real, career-establishing record.
I have the good fortune of the bar being kind of high — like, the vocal performances require the kind of intensity that is not common for a male voice. So my job basically was to hit it out of the park.
When I was a kid, I grew up [being] into the Yankees. I found out later in my career that [some] power hitters became fans of mine because they related to the intensity, and the power of [my] music.
I hope Aaron Judge is blasting some Michael Bolton to get inspired in the locker room.
[Laughs.] Everybody could use a lot more Aaron Judge.
When you look back at your catalog, which song — or songs — feel the most like the artist that you set out to be?
Probably a combination of a few. The biggest hit that I've had is "How Am I Supposed To Live Without You?" It went to everyone twice because I released it again. It was [originally] released by Laura Branigan, and it did really well with her.
About eight, nine years later, I released it myself as an artist compared to just being a songwriter. And something else happened — that version is much bigger than the first time around.
At the same time, "Said I Loved You, But I Lied" is one of my favorite records that I've ever made.
Why is that?
Mutt Lange was my producer, and he's always done something very different that makes the record itself stand out in the middle of these hit songs — and none of them specifically sound like a Mutt Lange record.
It's pretty amazing, the good fortune of finally doing what I love to do on my own terms. And that's what happens when you have enough success.
What's a standout memory for you from everything that you've done?
I had a chance to sing with Luciano Pavarotti. And I am a tenor — we don't use the term tenor or baritone or anything like that in pop music. But when a tenor hears another tenor on the radio, you stop what you're doing and you listen to how these high notes get sung and held for a long time. The control and the power that the great tenors had is something that really excited me, and I had the opportunity to work with all three tenors and do something that I had never, ever dreamed.
It took me about two months to learn Italian and to learn opera. I was up until 5, 6 o'clock in the morning, almost every night trying to absorb it all before this performance in Italy in Pavorotti's home city.
I can only imagine trying to actually sing something like that, let alone on stage, with one of the most iconic stars from that country.
It was very daunting. Exciting, like, otherworldly. But it was very, very daunting.
Pavarotti walked in after we were warming up the orchestra. It was an outside venue, an amphitheater, and Princess Di was in the front row. Bono was on stage during a song or two.
We began getting ready, and Pavarotti heard me singing with the opera, and he walked over to me. I was nervous. And he said, "I see you have been studying the tenor."
I said, "Actually, I've been studying you. And I don't know what I've been doing with my voice all these years." He smiled ear to ear and said, "You do not sell as many records as you have if you're not doing the right thing. Let's rehearse."
That was the beginning of our friendship.
How does the career that you've built compare to what you envisioned for yourself when you were first starting out in the business?
Sometimes I feel like I'm the Forrest Gump of the music business. Because each scene, I'm standing next to Stevie Wonder, or Ray Charles, or Pavarotti, or Paul McCartney, or somebody who's a part of my love of music and were a powerful influence on me. I never thought, One day I'd love to meet this person or with this person. It just happened. When it finally started happening, it just became surreal. Dream-like.
What's left on the Michael Bolton bucket bucket list?
I think there's definitely some more recording to do. There is also definitely more streaming television, film, comedy. And maybe it's a musical, maybe it's a film, I'm not sure, but there are a couple of projects looming.
At the same time, when we got offered to do the Lonely Island "Jack Sparrow" video, it was a surprise. So I'm kind of thinking that what's gonna happen it's gonna reveal itself, and surprise me again.
Do you think you'd ever do another Lonely Island thing, was that such a moment that you can't really repeat it?
I would do it in a heartbeat if the script had "funny" written all over it. That's the only sin you can have with comedy, is for it not to be funny. Then you can't get away with anything.
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