Living in L.A., what do you miss most about Baltimore?

Of course, I miss the “Baltimore CrabCakes,” and the Crabs from Fells
Point. I also miss my friends, family, and quiet drives through the city—whose
architecture looks like no other—while listening to music.

What Baltimore musicians do you admire?

There are so many great musicians from Baltimore, and I admire many of them
including: Mickey Fields (RIP), Mashica Winslow, Dennis Chambers, Tom Williams,
Whit Williams and his Big Band, Tim Green, Gary Thomas, Gary Bartz, Billie
Holiday (recordings), Cab Calloway (grew up and created his style here),
and Ron Pender.

In what ways has Baltimore and the
essence of the city infused your music?

There is a struggle inherent in the city that I think flows in ALL of the music
that comes from Baltimore—a hardness, passion, and desperation. The rock,
r&b, jazz, house, club and pop have a cathartic sound and an “all
in” emotional intensity that I think is a signature of our Baltimore
culture; there’s an urgency in our music. It’s very real, authentic, and pulls
no punches.

I have benefited from both the tragic sides and the classy
sides of the city, and they are both represented in my music. I’ve rapped in
songs about my mother’s struggle in the inner city, as well as my scholarship
at The Peabody Conservatory of The Johns Hopkins University. My whole life is
wrapped up in this city, and I rep it all over the world, wherever I go, and to
EVERY celebrity I work with—from Justin Timberlake to Jill Scott to Queen to
Jay-Z…they all know I’m from Baltimore.

I have a lot to prove. I’ve bussed tables in the finest
restaurants, been bullied in public schools, and worked for amazing lawyer
Billy Murphy Jr. I’ve played for the opening of the Ravens Stadium, when they
came to Baltimore with the Baltimore Symphony Orchestra and Stevie Wonder. All
of these experiences go into my musical compositions.

Your high school years were personally tumultuous. What effect did School
for the Arts have on you at that time?

I cannot say enough about The Baltimore School For The Arts!
It saved the lives of both me and my wife, Mashica. We met so many talented
people, teachers, and friends. It is a magical environment for a child to grow,
not be judged, and hone a skill that will set them up for the rest of their
lives.

Seeing your peers perform at such a high level inspires you to achieve great
heights! The school was a mix of all genders, races, ethnicities, social
classes, and backgrounds. This environment proved to be excellent in
stimulating cultural sensitivity and respect for others. Most students left
with a scholarship, some financial assistance, amazing academic scores, and a
90% chance of college attendance…what more could you ask for?

I NEVER got into a fight and this safe-haven allowed me to
focus on my studies despite my tumultuous circumstances of living in a drug
house on North Avenue. I was focused, and the school, through music, gave me
hope. My wife and I started the non-profit Music Motivating Minds Inc. because
of how the school helped us. We created this initiative for the youth of
Baltimore to help them set goals and learn self-esteem and respect for themselves
and others through music.

What are the pros and cons of working
with family on your Winslow Dynasty project?

This is a great question! It always causes me to giggle because anyone that’s
married knows the dynamics of working with a spouse can be particularly
challenging, especially when it comes to criticism. We are very blessed in that
Mashica and I were best friends long before we were married, so the respect and
love was at such a high level before romance entered the picture. We create,
build, and work amazingly well together. We can read each other’s minds, and
finish each other’s sentences—that’s the kind of love God gave us. She’s also
an amazing teacher and mother to my son Jedi. Jedi has such a heart and
compassion for helping others that he’s hard not to want to be around.

For me LOVE is such a necessary and healing component to
life that I could not imagine NOT working with family when it comes to
something as sensitive as music. 

Words on the page, and songs, do no justice in describing my deep love for
Mashica and Jedi. We love each other, we love our jobs, and we love to share
our experiences with others through music. I can’t think of any cons—Love,
Life, Family, Health, and Music…I have reached the mountaintop!

It’s refreshing to hear an album that
nods to so many genres/styles. Seems like you’ve always leaned in that
direction (or directions), and, in that respect, someone like Robert Glasper
reminds me of you. Where did you get that sense of musical inclusiveness? Where
is it rooted? 

That’s deep! It’s funny you should say that, because as an independent artist
most people would have to be from Baltimore to know that I’ve always recorded
in a synthesis of styles, mixing jazz, r&b, hip-hop, and classical
elements. Glasper is a colleague of mine, but I’d never heard of him when I was
making records in Baltimore, and he’s younger than I am. I grew up listening to
Michael Jackson and early hip-hop artists such as Run DMC, UTFO, and Whodini. I
also loved Chopin, Rachmaninoff, Mahler, Stravinsky, Schubert—the romantic
composers. I just can’t separate beautiful music by category.

When the time came for me to do my own music, I had no
qualms rapping over Shostakovich melodies and then playing a jazz solo over a
rap beat—I just feel limitless in that way, open. Gary Thomas, my mentor and
jazz teacher, has always used a synthesis of styles and incorporated computers,
multi-genre formats, and advanced jazz vocabulary into his work. I’ve inherited
a lot from him.

That musical inclusiveness also comes from living in
Baltimore, where you can experience a plethora of musical experiences and each
has its own subculture of icons and heroes. I lived on North Avenue and you
could hear Rakim blasting down the street from a car, then we’d go ice skating
in Mt. Washington and they’d be playing George Michael’s “Father Figure,”
my all-time favorite teenage tune. On weekends, we’d go skateboarding in
Lansdowne bowls while listening to Suicidal Tendencies, and at night ride by
The Paradox and dance to BMORE club music! The door was always open to
divergent musical styles in my world, and I was always bold enough to include
them all when writing.

I’m happy to see musicians like Robert Glasper win a Grammy
and receive radio airplay, because I have been fighting small-minded consumers
for over 20 years and his commercial success opens doors for all of us. Now,
with the invention of the iPod, Facebook, YouTube, and social media people are
more exposed, open-minded, and educated about the artistic possibilities in
creativity, and expression through music.

What’s most satisfying about working with
folks like Jay-Z and Justin Timberlake?

The most satisfying thing for me is the education I receive by being around
such talented artists and such savvy businessmen in Jay-Z and Justin
Timberlake. They are in peak form and at a ripe age, as am I, but they’ve had
more commercial success. I have the unique opportunity of observing the best in
their prime. I benefit from the lessons I see in their work ethic, discipline,
and tireless approach to perfecting their craft. 

Two special stories come to mind:

My wife and I always laugh and have a running joke that
“multi-millionaires” don’t get tired! On the set of “Suit & Tie”
video, which I was apart of with Justin and Jay-Z, many of us where cold and
tired from 20-plus hours of over 200 performance takes of the entire song. We
were dressed to the 9’s in Tom Ford attire at the Hollywood Bowl. But I noticed
Jay-Z and Justin were as excited and unaffected by fatigue at 1 pm as they were
at 2 am, and that blew my mind. Jay-Z even said to us…”Y’all tired”?
We said “nawww.” Justin had been dancing the routine for more than 8 hours,
take after take, just nailing the moves. And in dress shoes!

Another magical thing happened backstage when we did the Legends of the Summer
Tour in Baltimore at the M&T Bank Stadium last August 8, 2014. I’d
co-written the song on Jay-Z’s album
Kingdom
Come
with my wife MaShica and Grammy-winning producer DJ Khalil. I told
Jay-Z backstage about how much the song meant to me, my family, and my mom, who
died of AIDS in 2001 after suffering drug addiction. I loved my mom immensely,
and I thought it was serendipitous that he would write a rap about his mom on
top of my music and call it “I Made It.”

Jay said, “WOW, man,” patted me on the back in consolation,
and said “The universe was speaking.” We then went to prayer with the full
band, JT & The Tennessee Kids, and Jay-Z and I initiated the final shout
after prayer. We all joined hands and shouted in unison, “1, 2 , 3, MAMA I MADE
IT!” That was one of the biggest compliments to my mom, to God, and to my
city of Baltimore! I literally burst into tears and had to walk away from the
circle cause I’d never dreamed of making it this far in music from my humble
beginnings at Cross Country Elementary School in Baltimore.