Comedian T.K. Kirkland on laughter, loss, and life lessons

On April 21, the iconic stand-up comedian TK Kirkland will grace the stage at Milwaukee’s Turner Hall Ballroom as part of his highly anticipated “Catch Me If You Can” tour. Known as Hip Hop’s Comedy King, Kirkland has entertained audiences for over 25 years with his unique brand of raw, uncensored humor and insightful perspectives on relationships and adult life.

In an exclusive interview with HYFIN before his upcoming show, Kirkland shared his excitement about performing in Milwaukee for the first time as part of a standalone comedy event. “I’ve been trying to get to Milwaukee for 30-something years,” he said. I’m so excited to be rocking with Live Nation. I’m so excited to come there to really show my talents and elevate the game of comedy, so to speak.”

Throughout his career, Kirkland has worked with an impressive array of artists, including Easy E, Jay-Z, Timbaland, Cash Money, Ludacris, Teddy Riley, and Guy. He even played the piano in Gwen Stefani’s music video as she pushed a guy off the stage. “I was the guy they all looked up to,” Kirkland revealed. “They all went on to be successful. It was crazy. I was bigger than all of them at one time.”

Kirkland’s success in the entertainment industry can be attributed to his strong work ethic, business acumen, and what he calls “Comedy I.Q.” He explained, “Comedy I.Q. is like a great basketball player, great football player, most of those people. Comedy I.Q. is amazing.” This innate understanding of comedy has helped Kirkland navigate the industry and secure a groundbreaking deal with Live Nation, booking himself for tours up to 10 years in advance. “I always knew what I was worth,” he said. “I know what I’m supposed to get, and then I deliver.”

When asked about the current state of the comedy industry, Kirkland expressed concern about the lack of originality and the reliance on social media followers rather than talent. “A lot of comics don’t have a lot of material, so they gotta go on with what they have,” he said. “Then you got promoters who only book certain people based on their Instagram followers, not based on talent.”

Kirkland also touched on the importance of respecting the older generation of comedians who paved the way for today’s success. “I hate to see where comedy is going today, where all the trash talking and back and forth until all the young comics coming up. I really feel that young comedians should respect the OGs in the business,” he emphasized.

In discussing his approach to comedy, Kirkland noted, “I’m a street hustler who happened to be a college…Now I’m, I’m truly legit. I’m a true businessman.” He added, “As the career keeps going, I want people to know…how TK was one of the greatest hustlers in standup comedy.”

Reflecting on the impact of loss and death in his life, Kirkland shared, “Death is part of lfe. Death is a part of the contract that the universe gives you. And life only goes to the..strong. It goes to the people who understand you because you can’t be weak because it’s getting worse out here, the way people think, the way people move.”

He continued, “I’ve dealt with death my whole life since I was a youngster, I have no family. My dad drowned. My brother got murdered by the police. My youngest brother died of an aneurysm. My mom passed,  all this before I was 40 years old. So, it is always been me against the world until I had my kids and they’re about to do their thing, and  I’ve always just been going hard…”

Kirkland believes that experiencing loss can lead to a greater appreciation for life. “What death does do for you though? It makes you know one day it is your turn. Two, it also helps you to really appreciate your life and when loved ones start leaving around you. I swear, you start appreciating the leaves blowing. If you look out your window, seeing the birds or you cut your car off the sounds of the tires on the highway is amazing to you. That’s how. Amazing life becomes.”

He added, “A lot of people will probably never reach that part. And that’s like when I do my stuff on Instagram and social media, some people call me simp. Some people say they don’t know what he talking about. And I’ll always tell ’em, I say, yo, if you live long enough, if you truly live to be my age, one day, you’ll go, oh, TK Kirkland was right. Like, yo, he was right. That’s the thing that I love the most, if you live, if you live long enough, everything I’ve said on social media, people, one, they will say he was right. And I like that part.”

Looking ahead to his show at Turner Hall Ballroom, Kirkland promised an unforgettable experience for his audience. “The show gonna be off the chain,” he declared. “I just want everybody to tell somebody who knows somebody that got a car to make sure you come through because I’m coming to Milwaukee, and I want you. Don’t meet me there. Beat me there because it’s going to be one of the best comedy shows you have witnessed.”

As TK Kirkland continues his “Catch Me If You Can” tour, fans can expect to be entertained by his signature blend of humor, wisdom, and unfiltered honesty. With his second wave of fame as a relationship and lifestyle guru, Kirkland is poised to introduce his comedy to a new generation of laughing fans, solidifying his place as a true icon in the world of stand-up comedy. “I have never been to Milwaukee,” Kirkland said. “That’s what I’m looking for. I can’t wait to hit more. We about to be out here.”