Kenny Hailey is a shining star in the universe of celebrity grooming and is known for shaping the signature looks of A‑list clients throughout the entertainment and culture industries. With a fascinating career marked by artistic precision and a personal touch, Hailey remains humble, never forgetting his roots and remaining thankful for every opportunity that he has been afforded.
I had the privilege to chat with Hailey about his life and career, a history that will surely leave you inspired.
What motivated you to get into barbering?
Kenny Hailey: As a young man growing up in Los Angeles, Calif., I watched my maternal grandmother style the beautifully coiffed hair of her celebrity clients in the 1970s. Later I observed my mother style hair in her salon. My talent and curiosity for hair was inherited but I wanted to be excellent at my craft so I studied hard to become a skilled cosmetologist. As a cosmetologist, I wasn’t limited to barbering and grooming. I learned all aspects of cosmetology including hair, skin, and nails of both men and women. There was a time I styled hair for both men and women. It was my ex-wife Tanya who realized I was especially gifted at grooming men’s hair, and she encouraged me to focus my craft there.
How did you amass such an amazing roster of celebrity clients? Will you share a few names?
Hailey: There is only one way I can answer this question. God is the head of my life and through him all blessings flow, and Dr. Dre! Success occurs when opportunity meets preparation. I have worked hard to hone my skill, and one day I got an urgent call to come to a highrise on Wilshire Boulevard to cut Dr. Dre’s hair. We met and I felt his positive energy. Of course he loved the haircut and invited me to be his personal barber. I have been Dr. Dre’s barber for more than 30 years now. Dr. Dre has always been at the forefront of so many projects – music, television, film, and more. He has been generous to refer so many people to me. I don’t advertise; all of my clients are by word of mouth and based on my reputation.
My clientele is very diverse. Architect Frank Gehry is a longterm client who has also left a lasting impression on me. I first met him in a chance encounter when I was cutting designer and branding expert Peter Arnell’s hair. Frank came into the area I was using to groom Peter and jokingly demanded Peter get up so he could get a haircut. Frank liked the haircut, and now I see Frank weekly, and he imparts wisdom to me about his career, his marriage, and relationship building.
You were a highly sought after dancer at one point in your life. What was that experience like? What are some of the shows, movies, and commercials in which you performed?
Hailey: When I was in high school, my friends and I enjoyed dancing at parties. We performed routines that we choreographed and audiences went wild. Eventually we were booked for events and traveled the country on tour with up-and-coming recording artists and appeared in their music videos. I also toured with Motown. A keystone of my career was when I choreographed and danced in Sinbad’s HBO comedy special, Brain Damaged, which was filmed in Atlanta, Georgia. My daughters Tyler and Kameron got the dance bug too because they danced for many years until they were adults.
What is your favorite vacation experience?
Hailey: Rapper Eminem was preparing to headline at Wembley Stadium in July of 2014. I must note here that Eminem was making history by becoming the first rapper to headline Wembley Stadium in London, England. As he was preparing, Eminem asked Dr. Dre to make a surprise performance during the concert. Dre supported his protégé and agreed on one condition…Eminem had to fly out Dre’s barber, Kenny Hailey, for the event. I was flown out for the event and after the concert, I spent almost a month on Dre’s yachts sailing all over Italy and France. This was the first of many vacations I spent with Dre and his entire family aboard huge yachts, traveling all over the world. I made lifelong memories during these trips with Dre and his family. Dre is one of my closest friends and I cherish the more than 30 years of friendship we have. We always have a great time together full of laughs.
What are some of your hobbies?
Hailey: During my travels in Europe, I saw many locals travel around the hills and mountains on Vespa scooters. I was intrigued and imagined riding one through the Hollywood Hills and the Mulholland Drive. Upon my return from one of those vacations I bought a Vespa; I eventually owned more than 10 Vespas. I used them to commute to clients’ homes and enjoyed time with my daughters on them too. In 2024, a friend and restaurateur John Moshe invited me to ride in a charity motorcycle ride called the Distinguished Gentleman’s Ride (DGR), which raises money to support men’s mental health. I rode a Vespa at my first DGR, but soon thereafter, I purchased Triumph motorcycles and gained a new hobby. I now have two Triumph motorcycles that I use for my daily commute and for coffee runs on the weekends with my girlfriend Veronica. I also love Jeeps, and I’ve had more than I can count. I enjoy carving time out of my schedule to spend quality time with my daughters as they drive my 392 Jeep Wrangler, final edition Hemi. I’m just dad in the backseat smiling ear to ear. We ride around town and sometimes off road in Temecula with the top down, as we sing our favorite songs.
If you could go back in time and give the 15-year-old version of yourself advice, what would it be?
Hailey: I was a shy and introspective 15 year old with big dreams. I would tell 15-year-old Kenny to keep the faith and remain close to God, for he has an incredibly journey planned for you.
What’s next for Kenny Hailey? What are you looking forward to in the future?
Hailey: I have big plans for the future, but I prefer to move in silence. However, I am excitedly awaiting the birth of my first grandchild, Matteo. Learning that I would soon be a grandfather changed my life in ways I could never have imagined. I have focused on my health and fitness, and (I’ve) thought reflectively about the world I would want Matteo to live in and my role in bringing it to fruition. I’m encouraged by him and he isn’t even born yet. More to come…It’s all love.
