Blair Underwood's Transformation over the Years – 30+ Photos

From breakout star to husband to Broadway performer, the celebrated actor has gone through a sweeping transformation marked by age, wisdom, professional evolution, and a romantic twist that blindsided the internet.

For decades, Blair Underwood, 61, navigated a carefully balanced life that included a steady, upward climb in the glittering world of Hollywood and a long marriage with three children.

But in a move that sent shockwaves through his follower base, the actor stepped into a daring new chapter in 2023 that invited both glowing admiration and hushed speculation.

Underwood, born in 1964, made his industry debut in the energetic musical film "Krush Groove," which gave only a glimpse of what was to come. But it was his riveting portrayal of attorney Jonathan Rollins in NBC's legal powerhouse "L.A. Law" that carved his name into the hearts of viewers.

The show captivated audiences from 1987 to 1994 — the very same year he married his first wife, Désirée Acosta, in what many believed marked the beginning of a love story that would last a lifetime.

The Role of a Man

Acosta would go on to teach him far more than he ever imagined, not just about love, but about what it truly meant to be a partner.

In a deeply personal 2008 essay for Oprah Magazine, Underwood opened up about the love that helped reshape his identity and the moment that shattered his long-held beliefs about marriage.

He revealed that by that time, his parents had been together nearly 50 years, and he had always considered them his "heroes." But their love, while enduring, was built on a very traditional foundation.

His father, an Army colonel, was the sole provider, while his mother stayed home. As a boy, Underwood stepped into a surrogate protector role with his brother whenever their father was away.

They fixed what needed fixing, looked after the house, checked locks, handled the cars, and stood guard. That upbringing etched in him a very clear idea of what a man's role should be.

"I wanted to be her rock, her protector. If she had a problem, I wanted to solve it. I thought that's what was expected of me," Underwood wrote.

The Conversation That Changed Everything

But one night, during a late drive home when they were still engaged, Acosta shared something deeply painful from her past. It was an intimate and vulnerable moment, and all she needed was a safe space to be heard.

Instead, Underwood immediately responded with advice, suggesting ways to fix what she had carried. She turned to him and gently told him the truth: she did not want him to fix anything. She just wanted him to listen.

At that moment, he realized the instinct he had been taught, the need to step in and take over, was not love. It was control. That single exchange shook the very foundation of how he approached relationships.

Redefining Strength in a Partner

From then on, everything shifted. His connection with Acosta deepened, and so did his relationships with his mother, his sisters, and his closest female friends.

They began to confide in him more openly, knowing they would be met with quiet understanding instead of unsolicited solutions. He only offered advice if specifically asked.

In the same column, Underwood reflected on his parents once more. Even their traditional dynamic had changed with time. When his mother fell ill, it was his father who became the caretaker. What once had been rigid roles evolved with necessity and love.

He came to understand that no relationship thrives without flexibility. At the time of writing, he and Acosta had already shared 14 years together and were raising three children. And through it all, he remained committed to growing, learning, and listening, every single day.

A Career in Full Bloom

During the course of his marriage, Underwood's career was anything but stagnant. In fact, he flourished on-screen just as steadily as he seemed to off-screen, building a résumé that confirmed his place as a formidable force in the entertainment industry.

Through the rest of the 1990s, he carved out a commanding presence in major films like "Just Cause," "Set It Off," and the big-budget blockbuster "Deep Impact." He also took on recurring roles in the police drama "High Incident," showing his range across both action and character-driven stories.

The momentum only intensified in the 2000s. Underwood was featured in a wide array of high-profile projects, including "Rules of Engagement," "Something New," "Madea's Family Reunion" (2006), and the acclaimed TV dramas "Dirty Sexy Money" and "In Treatment."

His name became synonymous with polished, powerful performances, and he continued to push boundaries in films like "Juanita" and "Longlegs," along with television roles in "The Event," "Ironside," and "Quantico."

He even appeared in Netflix's gut-wrenching true-crime drama "When They See Us," and later shared the screen with Octavia Spencer in the riveting biographical series "Self Made: Inspired by the Life of Madam C. J. Walker."

As the 2020s dawned, he returned to his theatrical roots with the Broadway revival of "A Soldier's Play," but what came next was not just a role. It was an unexpected life shift.

The End of Nearly Three Decades

In a shocking turn that blindsided fans, Underwood and Acosta announced in 2021 that they were officially separating after 27 years of marriage.

The longtime couple shared the news in a heartfelt joint message posted to Instagram, revealing that the decision came after deep reflection and painful consideration.

"It has truly been a beautiful journey. Our proudest achievements are our three incredible children. Three souls to which God entrusted us," they wrote together in the emotional statement. "We continue to be awed & humbled by the blessings of parenting."

Despite the heartbreak, the pair presented a united front, pledging to prioritize their children and remain both friends and co-parents. The announcement strongly hinted at an amicable split, rooted in mutual respect rather than scandal.

They closed their message by thanking the public for their support and asking for privacy during this personal transition.

A Surprising Announcement and Backlash

Just one year after his divorce, Underwood sent the internet into a frenzy when he posted a glowing photo of himself and Josie Hart, arm in arm at a red carpet event. But it wasn't the picture that caused jaws to drop; it was the caption.

The actor revealed that Hart was now his fiancée, calling her the "most amazing, brilliant, beautiful, hilarious, thought provoking & insightful person [sic]."

"The future is crazy-bright Girl! None of us ever know where God will guide our paths. She's had my back since before I even became an actor. When a 41 year friendship slaps you in the back of the head & blossoms into romance, you stand up, pay attention & step forward in gratitude. Gently forward. It begins!" he added, radiating newfound love and excitement.

But the internet was far less enchanted.

Underwood's comment section quickly became outraged, with many netizens seemingly accusing him of crossing a line during his marriage to Acosta. The timing, and the revelation that Hart had been in his life for over four decades, raised eyebrows and fueled suspicions.

One person blasted, "Adulter and Adultress, leave one marriage to go into another, that's the way of the world [sic]." Another added pointedly, "He gets a divorce and a year later he marries his best friend. Something is off about that."

The most scathing remarks came from netizens convinced the friendship masked something deeper. "Left your wife of 23 years to cheat on her with your 'friend'. 🤢🤮 Lol! Let's see how it will go. Women never allow your husband to have a best girl 'friend'! He will cheat on you with her [sic]," one person warned.

Another echoed the sentiment bluntly, "Exactly why I don't trust that friend word."

Happiness Shines Through

Amid the storm of backlash, a few voices rose in support. One netizen cheered them on with bold enthusiasm, "She waited and Won, ya'll, don't be mad! When you're slow, you Blow!..and i was Never Slow [sic]!! 😝"

Another simply celebrated the moment, writing, "Congratulations, you guys are a beautiful couple!"

Underwood and Hart were officially married on June 24, 2023, in a lavish, sun-drenched ceremony at the Casa de Campo Resort & Villas in the Dominican Republic.

The actor revealed to People that he had played an active role in planning the day, which welcomed more than 100 guests, including familiar faces like Kim Fields and Malcolm-Jamal Warner.

But the magic wasn't just in the details, it was in the overwhelming emotion that swept through the evening.

The new couple exchanged vows beneath an arch adorned in roses, surrounded by family and friends whose bonds stretched back decades. One wedding guest recalled that everyone was crying, which was a reflection of the years-long connection between the two families.

"The deep emotions that were displayed during the ceremony, the lightness and fun of the reception, it all felt humbling because it all just fell into place," Underwood shared. "It was amazing."