Interview by Bret McCabe
The estimated 103.4 million viewers tuning into the Super Bowl LVI halftime show in February caught an enthusiastic love letter to 1990s hip-hop featuring Dr. Dre, Mary J. Blige, Eminem, Snoop Dogg—and Baltimore’s own Dontae Winslow (BM ’97, MM ’99, Trumpet). Winslow, playing his signature Adams trumpet, was making his third Super Bowl appearance, and follows it up this weekend with his third appearance working one of the other biggest nights of television: this weekend’s 94th Annual Academy Awards ceremony on ABC.
The Los Angeles-based Winslow has carved a multi-prong career as performer, songwriter and composer, orchestrator and arranger, producer, and conductor in popular music, jazz, film and television. Peabody Magazine caught up with Winslow to talk Oscars rehearsals, thinking in different musical realms, and working while parenting.
How did you first start working with Oscars musical director Adam Blackstone? Was it when you were both in Justin Timberlake’s band?
We actually met in 2005 when I was working with Queen Latifah and he was working with Jill Scott. We connected way back then and we’ve been partners ever since, doing music and arranging and being in bands. So we still work together and partner on things. When he got the call to be musical director of the Oscars, he put a team of orchestrators together—me, him, and our other lead orchestrator, bassist Derrick Hodge. And we just started knocking this stuff out. I actually started way back in December, putting compositions together, and then Derrick came on around February and we started putting together arrangements for scores, popular music, and some of my original music to accent the show.
We started rehearsing this week, actually, recording at Capitol Records with a 44-piece orchestra. It sounds so fantastic, but it’s different than any other Oscars show you’ve heard before.
You’ve worked a few Oscars programs before, but you’re pulling multiple duties this weekend.
Yeah—it was my third Super Bowl and my third Oscars coming up. I played with Justin Timberlake in 2017 and then Eminem in 2020. This time I composed original music for the program. I’m conducting. I did arrangements and orchestrations and programming. And I’m performing, playing trumpet. I had to make a list to keep track of what I’m doing because it was so many jobs. I’m doing six different jobs on one of the biggest TV shows on the planet.
Can you tell me what you’re performing on?
Specifically I can’t really say, but when you hear trumpet and you hear it soloed, it’ll be me.
How do you prepare for a gig like this?
It’s the most well-rehearsed show in Hollywood. There’s a very detailed list of what’s going to be done that night, and they run a very tight script. And things happen—people could walk up the steps and trip and fall. I studied the Oscars on YouTube to prepare for the show, and I noticed how long people took to present awards, how long people took to accept an award, and it ranged from 15 seconds to 25 seconds, from 45 seconds to up to a minute and a half. And in that regard, the program is flexible, and you have to be willing to change and adapt to what is happening in real life as a musician, arranger and conductor. But for the most part this show does stick to its script, unless somebody does something fantastic and wonderful such as thanks everybody in their home city.
Do you enjoy these kinds of big projects?
Let me tell you, I overjoy it. When I was conducting the orchestra during rehearsals yesterday I was crying and feeling so emotional. And the musicians—these are top Hollywood studio musicians and they were very appreciative of the spirit of unity, love, and passion I was trying to bring to it. Hearing them say back to me that they felt welcomed and they felt the love inside the music and the respect for tradition, that was the greatest compliment. What you’re going to hear from the screen is the love and passion for making music.
Next up you wrote the music for a play Phylicia Rashad is directing at the Center Theatre Group in Los Angeles, right?
She’s doing Blues for an Alabama Sky written by Pearl Cleage that opens in April.
It’s an amazing story and I composed music for it based on music of the 1920s. So these past few months, I’ve been dealing with music from the 1990s at the Super Bowl, this play is music of the ’20s, and the Oscars is music from so many different eras, European music, futuristic music from Dune—the realms that I have to walk in for my job are so vast and different. I’m also scoring a film starring Wesley Snipes and Tiffany Haddish that comes out in September, so that’ll be something to look forward to.
And you and your wife have been navigating all this with a newborn.
Which means we don’t sleep. [laughs] She’s been in my lap so often that what felt hard went past the difficult and into the lane of easy. I’m thinking, No composer has a seven-month child on their knees while they’re writing and listening and recording parts and trying not to make too much sound. But after a while, it became effortless.