This week on the Who Is Podcast, we sit down with one of the most outspoken, entertaining, and respected personalities in comedy and hip-hop culture—the legendary TK Kirkland.

Known to many as the "Gangsta of Comedy," TK has spent more than four decades building a career that goes far beyond telling jokes. From his early days touring with Eazy-E and N.W.A. to sharing stages with some of the biggest names in music, including Tupac, Jay-Z, and 50 Cent, TK has had a front-row seat to some of the most important moments in hip-hop history.

But TK's story doesn't stop at comedy. As an actor, entrepreneur, writer, and podcast host, he's built a reputation for speaking his mind, telling unforgettable stories, and dropping the kind of life lessons that make people laugh, think, and sometimes feel a little uncomfortable. Whether it's relationships, money, the entertainment business, or the realities of life, TK has never been afraid to tell it like he sees it.

With comedy specials like Are There Any Questions? and Who Raised You?, along with memorable appearances on The Breakfast Club, Drink Champs, VladTV, and his own TK Kirkland Show, he's introduced his unique perspective to multiple generations.

In this episode, we go beyond the comedy to talk about his early years in the entertainment business, his relationships with hip-hop legends, the stories behind the success, the mistakes, the lessons learned, and how he's managed to stay relevant in an industry that constantly changes.

He's funny, controversial, brutally outspoken, and always has something to say. And when TK Kirkland starts talking, you never know where the conversation might go.

This is the legendary TK Kirkland on Who Is.

This week on the Who Is Podcast, we sit down with one of the defining voices of Baltimore hip-hop—Travis “Bossman” Holifield. Coming out of Northeast Baltimore, Bossman first made noise as Jimmy Hash with N.E.K.—the Northeast Kings—before stepping out on his own and becoming one of the city's biggest independent rap success stories. His 2004 album Law & Order became a Baltimore classic, fueled by records like “Off da Record” and the Rod Lee-produced “Oh,” better known throughout the city as the “Baltimore Anthem” or “Land of the O.” Bossman's movement was built from the streets up. Local radio embraced the records, Law & Order moved more than 10,000 copies independently with initial distribution thru Unruly Records, and the buzz eventually caught the attention of Jermaine Dupri, who signed him to Virgin Records. His music would also become connected to the sound and culture surrounding HBO's The Wire, further putting a Baltimore voice in front of a national audience. But the Bossman story is bigger than a record deal. It's about what happens when a Baltimore artist builds his own movement, gets the attention of the industry, experiences the highs and setbacks of the major-label system, and keeps moving forward. In this episode, we go back to N.E.K., Law & Order, “Oh,” Baltimore radio, the major-label years, the people who helped shape the journey, and what Bossman has learned from more than two decades in the game. Baltimore knew the name before the rest of the industry came calling—this is Bossman on Who Is.

This week on the Who Is Podcast, we welcome one of Baltimore's biggest personalities and one of the most recognizable voices in comedy and radio—Jess Hilarious. Born and raised in Baltimore, Jess took the personality, humor, honesty, and unmistakable attitude of her hometown and turned it into a national brand. What started with hilarious videos and her breakout Jess with the Mess commentary on social media quickly grew into sold-out stand-up shows, Wild 'N Out, television roles including FOX's Rel, and appearances across some of entertainment's biggest platforms. Today, Jess is bringing that same unfiltered energy to millions of listeners as a co-host of the nationally syndicated The Breakfast Club, alongside DJ Envy and Charlamagne Tha God. And she's continuing to expand beyond radio and comedy as an actress, entrepreneur, and now author with 'Til Death Do We Parent, sharing her own funny, real, and sometimes complicated journey through parenting and co-parenting. In this episode, we take it all the way back to Baltimore and talk about the grind before the fame, going viral before everybody was trying to go viral, breaking into stand-up and television, navigating success, motherhood, The Breakfast Club, and what happens when the world gets to know Jess Hilarious—but Baltimore already knew who she was. Funny, fearless, outspoken, and always unapologetically Baltimore—this is Jess Hilarious on Who Is.