Musician Dontae Winslow Talks New Album, Playing With Justin Timberlake & High School With ‘Pac

Dontae Winslow’s trumpet melodies have been heard by millions of listeners, albeit unknowingly. Currently touring with Justin Timberlake’s band, The Tennessee Kids, on “The 20/20 Experience Tour,” having played for Timberlake and JAY Z on “The Legends Of The Summer,” and on releases by  Kanye West (“We Major”), Beyonce (“Ego”), amongst others, Winslow is a student and teacher of the game who’s seen it evolve while learning from the best.

“I feel like I’m in a fortunate place in music history. I was born in 1974,” says Winslow, a Baltimore native who went to high school with Tupac. “I got to see an important part of Black history make one of its biggest shifts before corporations got in and tainted it. Then I’ve seen it get torn apart. The blessing is it spreads culturally – everybody’s doing it, everybody can do it. But I remember a time when only people from the hood could sound a certain way, only people from the hood were fresh because nobody could see what we were doing and creating on the spot. I got to see jazz get separated, then come together with D’Angelo calling Roy Hargrove so that R&B was borrowing from the jazz world. I got to see pop merge with R&B, and R&B embrace hip-hop. I’m the same age as the history, I’m growing with it.”

As lead man taking his playing experiences and zeitgeist, Winslow assembled Winslow Dynasty and crafted a tight blend of jazz, soul, funk, blues and hip-hop showcased prominently on his latest record Enter The Dynasty. Life+Times caught up with Winslow to discuss his latest album, soul music, growing up with Tupac, working with Timberlake, D’Angelo, the Soulquarians and more.

Life+Times: There are some tracks on Enter The Dynasty, that are super, super funky, and then others are slower ballads. What was the vibe of the record as a whole?
Dontae Winslow: The first song is called “Baltimore Crabcakes.” It’s a real dirty, down and gritty blues, kind of like a Mississippi Delta, Chicago blues – BB King-style. That’s the first song I recorded with the band I use. I told Justin Timberlake, “The Tennessee Kids, we’re all a band, some of these guys are my friends, we play well together and are great musicians from different parts of the country, we just want to steal one night to record it.” It came out in one take and I was like, “Whoa, maybe I should start a record.” Kind of like that old school recording of the Motown days where you just get in the room, play live, and if you have a certain level of musicianship, it comes out like a record right on the spot. I took that concept and just did 10 songs. 80 or 90 percent of them are first takes. One song I might have used a second take. That’s the way a lot of the cats did it back in the day when they made classics. My goal was to make classic songs, not thinking about genre per se, but thinking about the emotion of Black music and how it’s recorded, how it’s done. Get great musicians in a room, get a great melody, then put your heart and soul into it. That’s basically how I came up with the concept of Enter The Dynasty.

L+T: How were the creative and recording processes? You recorded with your spouse on some of these?
DW: The creative process – everybody walks around with iPhones these days and I use it as a great writing tool. Like, sometimes a melody will come to me in the middle of the night or during the day, and I like to sing into the phone. That’s that raw, natural, intuitive way for me of writing music. Whenever I do that, it seems like it becomes a real song. I’ve produced for a whole bunch of people, but in this style of music, soul music, I wanted to approach it from a live performance perspective. So for me, the live band part was really important. My band consists of me playing trumpet and I [also] rap. That’s my niche, or my contribution to American history; I’m one of the first, if not the first, trumpet player-slash-rappers. I’ve been doing that about 20-25 years. My wife sings and she writes songs, so she’s the other half of the duo Winslow Dynasty. We write songs and have been performing together for years, so when me and her get together we have that synergy like true jazz musicians who can just respond to each other or make up something on the spot.

L+T: Were you always rapping?
DW: I’ve always rapped. From 1985 on I got hooked, we all did beats on tables at lunch and listened to the Fat Boys, Run DMC, Kurtis Blow, [and] Furious Five. I was always the best rapper in school. That’s before Rakim, before Nas. Once you heard Rakim in 1986, it was like, “Oh my God, I gotta step my game up and sound like Rakim.” Then Nas around ’92: “Oh, he’s got the complex analogies, all these hyperboles.” For me, that’s the two biggest times rap changed other than West Coast rap when stuff got gritty. Whatever you were doing, you knew you had to switch it. For me, [there’s] Rakim, Big Daddy Kane, Nas, then everything else is some kind of culmination of that. I had been doing it the whole time, then I started playing trumpet when I was around 12. One day this great jazz musician took me on the road – he was very innovative, ahead of his time – he was very impressed with West Coast hip-hop and A Tribe Called Quest. So he started using that in his jazz. In the ’90s, he said, “You’re a young cat, I see you rap and play trumpet, I want you to do both at the same time.” I said, “I can’t do that, that’s not a good look for me.” He said, “Listen, the gig pays $1,500 a week.” I said, “Count me in.” So, my first tour was 1992 going to Germany. I was very scared and nervous, but Europeans were so open to it; this is way before Lauryn Hill, Kanye, the artsy side of music was acceptable. This was when Eazy E just popped off. Tribe was in there, but they weren’t really playing instruments. Since ’92, I decided I was gonna rap and play trumpet and one day everybody will understand. One of my primary influences, Tupac, went to the Baltimore School For The Arts with me. When I was in the 9th grade, he was in 12th. He used to write all these raps about political struggle. He was the man at school, him and Jada [Pinkett-Smith]. He and Jada were the most popular in high school and I was like his little brother, so when they graduated, I kind of became the most popular. I always looked to him, wrote him letters and kept in contact with him when he went to L.A. He came back to school with all these Oakland views, Raiders jackets in all black… that’s when gangsta rap started popping off. His mother used drugs, my mother used drugs. That’s like a Baltimore thing. That’s what we both came from and what we had in common. So he used to always call me and be supportive. [A few] years later he did All Eyez On Me, had the “Thug Life” tattoos, and I was like, “Whoa!” He came back to the school, did a show for the kids, and we were up talking all night. He became an icon right before my eyes. People were doing tricky, slick stuff, Kriss Kross, etc., but he said, “Always write stories and write about what you’re really going through.” That’s the primary focus of my style now, jazz, rap or whatever.

L+T: On “Summer Cookout,” you brought in ?uestlove and Roy Hargrove, and it sounds like something that could be straight out of the D’Angelo Voodoo sessions.
DW: “Cookout” is a real soulful [record]. I was doing a gig with Jill Scott one day, playing on a vocoder and came up with the first three chords of the song. I said, “This sounds like a straight Virginia, Maryland southern cookout vibe right here.” That was the basis of the song. My friend Adam Blackstone was playing bass. We worked out the song form and I started playing my trumpet through, like, a wah-wah pedal and it sounded cool like a guitar. You know, when you’re doing a song, you start to hear people on it. So, at first it wasn’t like D’Angelo or Voodoo, but since he’s from Virginia – and if you go towards gospel quartet, that’s the sound of the South, the sound of Black music from the church when it mixes with R&B and secular – that’s why it has that vibe to it. I went to New York, my friend Roy Hargrove played on it – he’s one of my mentors. We harmonized with each other and kind of traded solos on it. There still weren’t drums on it yet. Then I went to ?-uest, let him hear it, and he was like, “Let’s do something.” It’s just a coincidence that we all worked at one time for D’Angelo, so you have ?uest from that school, my friend JK, I was in his band when Voodoo first started, and then Roy Hargrove replaced me. So, four people in the band were a part of it, then it has that southern gospel quartet style.

L+T: Talk about playing with Justin Timberlake on “The 20/20 Experience” Tour and bringing that soul element to the mainstream. The Tennessee Kids are considered one of the best bands in the world.
DW: First of all, it is one of the best bands if I may say so myself. I say that because other people – friends of mine who play jazz – tell me that. They say, “Y’all are the best band in music.” That’s subjective, of course, but to hear that over and over – the fans really love the energy of the band, then individually, everybody’s a beast on their own. Everybody’s a real passionate and emotional cat; I love these guys, they’re nice guys and they’re good men. You couple that with good musicians who care about what they’re doing. So, you’ve got 19 people who think it’s life or death for his part, and you put it together, it’s like the Bulls in the ‘90s. The best of the best, they’re hungry, they’re making paper but they act like they ain’t got no paper – that’s how they play. That’s how this band is. We practice together, we’ve done TV shows, other tours, so we’ve always played together it just so happened that we landed with Justin. He heard it and he was amazed by it. Him being a student of Black music, music in general, the history of pop from Michael Jackson and James Brown, he knows what he’s listening to. He knows D’Angelo, Roy Hargrove, he knows what he wants it to sound like and these cats give it to him. I appreciate the fact that he would record that would speak to soul music and the artistry and creativity of what Black people have created over the last 80 years. In the 2000’s, a lot of guys try to do the European pop thing and follow trends. With his large fan base, for him to bring music back to this, for me, is good. That brings everybody back to what I think is still essential to soul music: the holler, the soul, the grit, the struggle. Not a lot of electronics or “four on the floor” in this record. Some of it sounds like straight church gospel quartet, mixed with pop sensibility and melody, but the grit of it is still live instruments; hard, with that underlying urban vibe that I think has been lost for the last ten years. It’s a good situation for me, musically, and I think it’s a good thing for people ears to get re-trained back to this sound.

Enter The Dynasty is available February 11. For more information, check out his site here.