Careers rarely go according to plan. In Job Hacks, we shake down experts for the insights they cultivated on their way to the top of their field.

Name: Frank Simms

Original Hometown: Stamford, Connecticut

Job: Frank Simms is a singer, session musician, voice actor, composer, and vocal arranger. He toured the world as a vocalist on David Bowie’s Serious Moonlight Tour and Billy Joel’s Innocent Man World Tour, sang with Carly Simon on her HBO Martha’s Vineyard Special, and with Roger Waters during the Hurricane Sandy Relief Benefit Concert. He’s also appeared on The David Letterman Show, Saturday Night Live, and Conan. And, oh yeah, he’s the Kool-Aid Man.

You’re like the Zelig of the voice world. How were you able to land so many different amazing opportunities over the course of such a long career?

Once you work with someone of [David Bowie’s] magnitude, everybody else wants you: “Sing on my record, sing on my record!” So we can go on a bunch of people’s records just by virtue of working with David Bowie.

A lot of the artists you’ve worked with have been extremely different — not just in music, but in personality. Did each one take some time to adjust?

I got to be on top of the ladder right from the beginning, with David. Then, when I worked with Billy Joel, I thought, “This will be fun! I’ll be in Madison Square Garden and going to Tokyo!” But once I actually did it, it was different. With David, all these gigs were cosmic. I don’t know if I can say that much about anybody else.

How did the gig with Saturday Night Live happen?

I was friends with G.E. Smith, the guitar player. At one point G.E. called me and said, “Frank why don’t you come down and sing on Saturday Night Live?” So I sang with him. And then somebody else would call me and say, “We want you to sing on this skit,” and little by little I’d do more. You get this feeling like “I belong here.” It’s so disciplined and specific. You know what you have to do and you don’t do what you’re not supposed to do. You show up, you’re on time, you know where to go, and you can wander around, and don’t try to talk to the big star. If you’re there long enough, you get to understand the rules: what’s done and what’s not done. People get comfortable with it. Lorne [Michaels] is very loyal. He likes to keep his good people almost until they die.

If there’s a musical number they’ll usually call me and five or six other people, depending on what they need. It’s fun! It’s a good gig. Everybody is always on his best behavior and at the top of his game. You feel like a real pro.

Did you expect some of the things you’ve done to take off the way they have — the Kool Aid man, for instance?

I really didn’t. I could do voices, I could sing well, I could sing personalities and do character voices, so they would call me. “Frank we need a Louisiana blues guy,” or “We need an announcer like the I Love Lucy Show.

Were the voices something you could always do, or did you develop that over time?

They had a Kool Aid guy, but at one point, they wanted him to start doing dialogue and actually say stuff. The guy said, “I’m only used to saying ‘Oh yeah.’” So I auditioned. That was a complete fluke that they chose me. Like in any audition — “Oh you chose me? That’s great, how lucky am I?” There’s no rhyme or reason to it.

How many times do people approach you quoting your previous work?

Many times. That’s been the most famous voice I’ve done — besides the hits like “Let’s Dance” and “Material Girl” from Madonna. I sing that robotic voice, “Living in a material world.” There are certain little nuggets that I happen to be lucky enough to perform on. You say one word and people say Oh, I know you!” I don’t mind, it’s fun.

What was that experience like — working with Madonna on “Material Girl”?

She’s a phenomenon, but not the same as David. She’s got a really good ear and a good eye. But I would never joke around with her. Never. Whereas David was like, “Let’s talk.” That’s not her. When we were in the studio, she would say, “time is money and the money is mine.

Do you think it would be possible in today’s music world to have the career you’ve had?

Probably not. In those days they were using a lot of session people. They wouldn’t be calling me, even if I was at the top of my game; it’s the style today. There’s the entire hip hop world, which completely passes by anybody like me. I could emulate it. I could emulate an opera guy or any number of things, but they don’t need me. Kanye West would have no need for me, and that’s who’s working. My stuff with David Bowie and Madonna and Billy Joel and Carly Simon and Jeff Beck and Cyndi Lauper — that was the ‘80s era. It wouldn’t happen today.

All the commercials I audition for these days say, “We don’t want an announcer type.” They want it to sound everyday and natural — not an announcer or an actor. I can do that, but will they choose me or somebody else? It’s such a flip of the coin! “His voice is more raspy, he speaks quicker, choose him.”

So that’s what’s happening. And so much of the work is non union! All of the work that I do has union support, which means I get a contribution for my pension and health. There is a written contract. Now non-union producers say, “Come in to do this Coke commercial and I’ll give you $500.” What they could conceivably do if I agree is keep me there for five days! With the contract, it was like, “These guys are working for one hour for this amount of money, when it goes on air, they’re getting residuals.” You sign it, and there’s your contract.

So about 75% of the current commercial work is non union. Celebrities participate because they want residuals. Actors like David Duchovny wants the Cadillac-type gig, and companies are eager to bring in celebrated actors.

What advice would you give a young person getting into the business?

I tell people who are working today, “You better save every nickel because you’re going to blink your eyes and it’s going to be gone.” Nobody would have told you that 30 years ago. Nowadays you’re on one or two commercials for six months and then they move on to the next guy. That’s the nature of the business now.

Younger people would accept $1500. They might do it for four or five days and they don’t have much choice because they have to pay the rent. Whereas in my day, most gigs were like, “this is a $20,000 Cheerio gig, this is a $40,000 Alka Seltzer gig.”

Everybody wants to be on TV, everybody wants to be in the movies, everybody wants a record contract. People have tons of talent. We have a stadium full of kids who want to sing like Taylor Swift. And yet the standard of excellence has lowered so everybody who’s not excellent can jump in the fray. And people who are excellent may look around and say, “I don’t want to get involved in that because I’m better than that.” The quality is so low.

During the days when I was working, you had to kick ass. You knew, “if I’m not good, I’ll never work again.” You had to raise your level. You mentality, voice, concentration, and dedication had to be at it’s peak.

Where do you think that excellence is now?

Right now I think it’s happening with TV. You get shows like Better Call Saul and Breaking Bad, that’s the standard they’re trying to reach now with writing and performing. Actors you’ve never seen before are winning awards. Netflix, Amazon, that paid content programming — since there’s so much of it, if it’s not great, you’ll get booted out! That’s where the edge is now.

What’s next for you?

I’ve written an entire diary from the first day of rehearsal [with David Bowie] to the last gig in Hong Kong. I always had a plan to publish it in some way. I’ve had an editor help me over the last two or three years. But the book never progressed beyond, “well let’s see what that looks like.” We’ll see what happens.