In the season finale, Donnie talks with comedian George Wallace (not to be confused with former governor of Alabama, George Wallace). George dives right into his adventures in show business, including his groundbreaking 1980 appearance on the Tonight Show with Johnny Carson, who rarely featured Black guests at the time. George also reminisces on his close friendship with Jerry Seinfeld and how they ended up as roommates when they first started in the New York City comedy scene.

In this episode, Donnie talks with close friends, R&B songwriting duo Jimmy Jam and Terry Lewis. The three of them go way back, but not many people know that they were introduced to each other by none other than Donnie’s mother! They discuss Jimmy and Terry’s experiences in the music industry and their favorite memories of the late, great Prince. As a bonus, Jimmy reveals the importance of creating music and how it impacts his daily life.

In this week's episode, Donnie sat down with the one and only Maya Milan, a rising singer from the DMV area who finished as the runner-up in BET's The Next Big Thing. Maya's career kicked off with a fantastic start, beginning with childhood. She reveals who her biggest music inspirations are, including R&B icons Keyshia Cole, Mary J. Blige, and Whitney Houston. Maya reflects upon her youthful days of singing in her church and its influence on her career years later.

In this episode, Donnie speaks with J. Prince, a god in the hip-hop industry. They discuss the rapid changes in the music industry landscape in recent years and go over some of his past work. J. Prince gets deep and shares reasons why he believes everyone deserves a second chance—a philosophy reflected in his body of work. https://youtu.be/OXWXnE4mNNQ

In episode six, Donnie sits down with Master Gee and Wonder Mike of The Sugarhill Gang, the creative masterminds behind "Rapper's Delight.” The creators of the first-ever US top 40 rap hit, Master Gee and Wonder Mike, share some unique perspectives on the state of hip-hop today and examine how hip-hop can provide social commentary. They also dive into the group's New Jersey origins and vote on who they believe to be the greatest rapper of all time.

In this episode, chart-topping singer-songwriter K-Ci of the reunited quartet Jodeci joins Donnie. K-Ci spills about his musical origins singing gospel music in Baltimore and divulges rare tales of his adventures as a '90s icon--many of them involving his brother, JoJo. Later, K-Ci breaks down his wild experience driving from Charlotte to New York with no money to pitch Jodeci to MCA Records.

In today’s episode, Donnie speaks with singer-songwriter Regina Belle, a wonderful friend since 1989. They talk at length about Aretha Franklin and what her music meant to them, as well as the changes in the music industry Regina experienced since starting her career back in the late 1980s. They also explore Belle’s personal life, including her triumphant battle with a brain tumor, her experience of winning a Grammy, and the enormous rise of her fanbase as a result of "A Whole New World" (one of, if not, the most successful Disney song of all time).

Donnie Simpson sits down with Tichina Arnold: the beloved star of many iconic television shows, such as Martin, Everybody Hates Chris, and the award-winning The Neighborhood on CBS. Tichina dissects her career path, tracing back from her start at the Billie Holiday Theatre in Brooklyn through her current endeavors--even discovering unexpected fame in Brazil. They also reveal the joys of show business and their travels to Jamaica, ending with a passionate discussion about horoscopes.