Cuba to Hollywood: The Christina Milian Story on R&B Money

Christina Milian joined hosts Tank and J. Valentine on the "R&B Money" podcast for an intimate, wide-ranging conversation that chronicled her artistic journey, family roots, personal struggles, and the come-up that defined her early years in the music industry. From her beginnings in Maryland to signing a record deal in Hollywood, Milian reflected on the highs and lows of her career with honesty, humor and gratitude.

The episode opened with the hosts celebrating Milian's multifaceted career—from singer and actress to entrepreneur and mother. Milian responded with warmth, noting that despite the accolades, she's always remained grounded, a trait she credits to her Cuban-American upbringing. "I'm Cuban, so I come from Cuban descent," she explained. "But Cuba is like a melting pot... from what I'm told, it's Spaniard, feels very Italian if you ask me."

Milian reflected on her childhood in Maryland, where her father served in the military. Her parents were young when they had her—17 and 18 years old—and she grew up surrounded by music, ambition, and a relentless drive to succeed. She shared early memories of performing for family and being drawn to musical theater. "I was always singing," she said. "Even when I’m having an argument or a conversation, I don’t even notice I’m humming or I’m singing."

That drive to perform eventually led her to musical theater in Washington, D.C., where she landed an understudy role at Ford's Theatre. She remembered memorizing every line of the production and ultimately stepping into the spotlight when another cast member fell ill. "I just felt the energy of being on that stage... it was invigorating," she said.

Milian's big break came at age 13, after performing in a play at the Pantages Theatre in Los Angeles. Talent agents took notice, urging her to stay in L.A. Her family returned to Maryland briefly to care for her ailing grandmother, but after her passing, Milian and her mother made the bold decision to relocate to California to chase Christina's dreams. "We just tried it out, L.A. for a second," she recalled. "We said, 'OK, six months, let's see what happens.'"

What happened next was a grind filled with small wins. Living at the Oakwood Apartments, known for housing aspiring artists, Milian began recording demo tracks and meeting industry producers. She worked with Spanky and Charles in their apartment studio and was eventually introduced to Rodney Jerkins. "He invited us to the studio," she remembered. "That was the first time I experienced music that way."

Milian began crafting her identity as an artist during long studio nights watching Jerkins work with Brandy and Whitney Houston. Despite being teased early on for singing in a "white" style, Milian persisted and found confidence in her voice. She started taking music business classes at Valley College and landed a $25,000 record deal offer from David Foster's camp—which she ultimately turned down in favor of exploring bigger opportunities.

Her pivotal moment came during a trip to New York, where she met with major labels and performed her original song "What You Gonna Do." Island Def Jam signed her after a powerful a cappella audition. "The day I finally signed my deal... we had to push our car to the attorney’s office," she said, laughing. "There was smoke coming out the car. But we signed a deal for $125,000."

That moment came after a season of hardship. Milian and her mother had struggled financially following her parents’ divorce. With no money for rent or food, the family leaned on each other, finding solace in faith and resilience. "We made this promise to each other on that walk back home that we were going to sacrifice... to focus on my career," she said.

Her breakout as a recording artist came in 2000 when she featured on Ja Rule’s "Between Me and You," a collaboration orchestrated by Irv Gotti. "It was like overnight," Milian said of the success. "I didn’t really know that it was blowing up like that." The single charted, and the accompanying video added to her growing visibility.

From there, Milian traveled to Sweden and Norway to record her debut album. Working with top-tier producers like Max Martin and Bloodshy & Avant, she also began developing her songwriting skills. One of her first compositions, "Play," was ultimately given to Jennifer Lopez. "They were like, 'Do you want to give it away?' I was like, 'Hell yeah,'" Milian said, laughing. "I didn’t like the song like that."

She kept "AM to PM" for herself, which became her debut solo single. Although the song dropped around the time of the 9/11 attacks—a moment that shifted the music industry—Milian was already making a name internationally. Her performances caught the attention of Johnny Wright, manager to *NSYNC and Britney Spears, who began co-managing her career alongside her mother.

Milian’s acting career also took off. She starred alongside Nick Cannon in the 2003 teen rom-com Love Don’t Cost a Thing, a reimagining of the '80s film Can’t Buy Me Love. She was cast after a general meeting with the film's director, Troy Byer, who offered her the role on the spot. "I had been auditioning my whole life... and they said they want me to do this movie," she said. "It happened so fast."

With momentum building, Milian returned to music and began searching for her next hit. She found it with "Dip It Low," a song written by Teedra Moses and produced by Poli Paul. "The first song they played was 'Dip It Low,'" she said. "I looked at my mom and we both said, 'That’s it.'"

Despite facing an abusive relationship at the time, Milian credited her support network—especially her mother and label team—for helping her refocus. She flew to New York to record, left the toxic relationship behind, and fully stepped into her artistry.

Milian spoke candidly about the challenges of the modern music industry, including the shift from music videos to digital content. "Back then, doing a video was special," she said. "Now it’s like people just shoot something on their phone." She noted how music videos once made superstars, referencing artists like Beyoncé, Chris Brown, and Kendrick Lamar who continue to invest in visuals.

As the conversation wound down, Milian reflected on her gratitude for coming up during what she called a "golden era." From grinding it out in Oakwood apartments to performing on global stages, her journey is rooted in passion, perseverance, and belief. "There was no giving up," she said. "I was not giving up."

Her story, as told on R&B Money, is one of humble beginnings, spiritual grounding, and the type of hustle that defines an era of music that feels increasingly rare.