Randy Waldman (all photos courtesy of Randy Waldman)

Musician and Pilot Randy Waldman

For decades, he has been a pianist and arranger for artists ranging from Sinatra to Streisand. He's also a popular helicopter instructor.

Grammy-winning pianist and arranger Randy Waldman is one of the most successful musicians you’ve probably never heard of. He’s also one of the most popular helicopter instructors in Los Angeles. In 2003, he set a helicopter speed record in a Bell 206.

A native of Chicago, Waldman was 21 when he went on tour with Frank Sinatra. For the past 38 years, he has performed with and arranged for Barbra Streisand. He has recorded with and arranged for artists ranging from Michael Jackson to Dolly Parton to James Taylor, and has performed with such stars as Billy Joel, Stevie Wonder, and Eric Clapton. His production credits include Patti LaBelle, Kenny G, and Olivia Newton-John. You can hear his music in dozens of major motion pictures, including Forrest Gump,Mission Impossible, and Titanic. His own latest album, SuperHeroes—which includes a track that won a Grammy this year—features guest appearances by a veritable who’s who of jazz, including pianist Chick Corea, guitarist George Benson, and trumpeters Wynton Marsalis and Randy Brecker.

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He told us in 2015 that he would never retire. Apparently not, because the now 79-year-old singer/songwriter has announced tour dates for summer and fall.

Waldman sporadically plays with a pickup band around Los Angeles, but he has no aspirations to ever be a headline act. “I wanted to be a studio musician,” he says. “I just thought it was very cool to be able to one day be a jazz guy, the next a country guy, the next a rock-and-roll guy. I loved the diversity.” 

As much as Waldman enjoys music, he loathes the idea of teaching it. “Wrong notes are like hearing fingernails on a chalk board,” he comments. “I just don’t have the patience for it.” Teaching helicopter flying is another matter. “It keeps me interested,” Waldman says. “My students are trying to kill me every second. It’s great.” 

Randy Waldman and Barbra Streisand
Randy Waldman and Barbra Streisand

How did you end up playing for Sinatra? 
Frank’s piano player was also his conductor, and Frank decided he wanted him to only conduct. The contractor they called [to find a replacement on piano] was my next-door neighbor. I really didn’t know that much about Sinatra, so I just said, ‘OK, that sounds like fun.’ 

At the first rehearsal, we were all playing and waiting for Frank. The phone rang. The conductor answered it while we kept playing. He came back and said, “That was Frank. He says you guys sound great.” So Frank never showed up, and the first time I played with him was on a big stage, just him and me, with no rehearsal at all. 

How did you meet Streisand?
I got a call to do a Streisand session after a friend had recommended me. And somehow, it’s been 38 years of working on every movie and record she’s done since. I was co-arranger for her version of “Somewhere,” which won a [1985] Grammy for the arrangement. 

How did you get interested in flying? 
In 1989 I was riding my bike past a field where people were flying radio-controlled model airplanes. I asked a guy there if he could teach me how to fly them. He was an American Airlines pilot and while he said he couldn’t teach me how to fly radio-controlled airplanes, he could teach me how to fly the real thing. So I said OK. Before you knew it, I was flying two or three times a week and got my fixed-wing private, instructor, multi-engine, and commercial ratings. 

And then you progressed to helicopters?
A few years later, I was touring with Streisand and we were all staying at this luxury hotel. She got sick and canceled the concerts but said the band could stay at the hotel for the week. I could see helicopters doing pattern work at the airport near the hotel and decided to take a lesson there. I was hooked right away. Airplanes need airspeed to fly. The helicopter was a magic carpet. It just picked straight up. So I became passionate about it. As soon as I got my private helicopter rating, I bought a Bell 47 and later I got a Hughes 269. 

Flying a Bell 47
Flying a Bell 47

Is it easier to teach a fixed-wing pilot to fly a helicopter as opposed to someone without flying experience? 
Yes and no. Fixed-wing pilots understand communication, navigation, and keeping an aircraft oriented on the horizon. I teach a lot of airline and corporate jet pilots. And because of all their experience, they think flying a helicopter should be easy. They can get really frustrated, because once a helicopter slows down, the physical skill needed to control it is completely different from the skill set that they have. They are expecting to be really good at this only to discover that they are no better at it than someone who has never flown. Below 30 or 40 knots, a helicopter is completely different from an airplane. 

Arguably, the hardest maneuver to master in a helicopter is the hover. Is there a secret to teaching it? 
Not really. The more relaxed you are, the easier it will become. But when you are doing something that is completely foreign, when the machine is flailing all over the place, it is hard to relax. Just relax as much as you can, don’t put any pressure on the controls, and don’t look down. The further you look out, the more you use your peripheral vision, the easier it will be. If you are looking down, you are going to try to correct for every tiny movement that the helicopter is making. You don’t drive a car by sticking your head out the window and looking down at the highway centerline. You drive looking out ahead. It’s the same thing. 

Do you have a favorite helicopter? 
The [Robinson] R22 is fun because it’s almost like a little jet pack: with every move you make, you feel the results almost instantly. But it’s a blast to fly a big, expensive turbine machine with a million bells and whistles on it, too. The [Airbus Helicopters] A-Star is a blast because it’s big but also powerful and responsive. I’ve also flown a 1950s tandem rotor Piasecki H-21, the helicopter they call “the flying banana.” That’s probably the most fun helicopter I’ve flown recently because it’s so big—15,000 pounds—and vintage.


Name: Randy Waldman

Born: Sept. 8, 1955 (age 63) in Chicago 

Education: Main East High School, Park Ridge, Illinois

Occupation: Pianist, arranger, conductor, and composer. Helicopter instructor.

Personal: Married. Lives in Los Angeles. Hobbies include trumpet, drums, magic, photography, and studying the medical college admission test exam book. (“I’d love to be a surgeon, but I’d be 110 by the time I finished medical school.”)

This interview has been edited and condensed.