Celebrating her milestone birthday in style, Ms. Lauryn Hill marked her 50th year surrounded by an intimate circle of family and friends, catching her by surprise. The special occasion unfolded on Monday, May 26, 2025, at the exclusive FlyFish Club, transforming the venue into a lively celebration filled with music, dance, and premium cocktails. Among the drinks served was Crown Royal’s rarest offering, the 31-Year-Old Deluxe variant, adding a touch of luxury to the event.
The guest list boasted notable personalities such as Rapsody, comedian Dave Chappelle, Rah Digga, and others. A memorable moment captured on social media by photographer Walik Goshorn features Chappelle delivering a heartfelt toast, which resonated deeply with attendees.
“Being 50 and still feeling vibrant and beautiful is no small feat,” Chappelle declared, earning enthusiastic applause from the crowd.
“We’ve been through so much together-survived hardships, celebrated victories-and tonight, we stand here as friends, family, and colleagues. I traveled all the way from Los Angeles just to be part of this moment. Missing it was never an option. I cherish you all. Happy 50th birthday, Lauryn!”
Ms. Hill, now in her fifth decade, continues to defy expectations. Earlier this year, she made her debut at the Met Gala donning a striking yellow double-breasted suit paired with a classic Hermès Kelly bag. She also graced the stage at the 2025 Jazz in the Gardens festival, reaffirming her status as a musical icon. Her influence remains evident as she recently celebrated the success of Doechii, the Grammy-winning artist for Best Rap Album, whom Hill mentored and supported since her breakthrough in 1997.
Explore highlights from Ms. Lauryn Hill’s 50th birthday bash below.
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Exclusive Celebration at FlyFish Club
Photograph by Tiffany Nolasco and Mustafa Hooten for Crown Royal A.J. Calloway joins the surprise birthday bash for Ms. Lauryn Hill at FlyFish Club on May 26, 2025.
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Family and Friends Gathered in Celebration
Photograph by Tiffany Nolasco and Mustafa Hooten for Crown Royal Ashley Newby and Shelby Giles were among the close-knit group celebrating Lauryn Hill’s milestone at FlyFish Club.
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Atmospheric Vibe and Signature Cocktails
Photograph by Tiffany Nolasco and Mustafa Hooten for Crown Royal The event featured signature Crown Royal cocktails, elevating the celebratory mood at FlyFish Club.
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Vibrant Ambiance
Photograph by Tiffany Nolasco and Mustafa Hooten for Crown Royal The lively atmosphere was complemented by elegant decor and lively music, making the night unforgettable.
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Comedic and Cultural Highlights
Photograph by Tiffany Nolasco and Mustafa Hooten for Crown Royal Comedian Dave Chappelle delivered a humorous and heartfelt toast, celebrating the journey of turning 50 with wit and wisdom. Accompanying him were Mr. and Mrs. Malcolm Ellis, adding to the night’s star-studded lineup.
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Family Legacy and Musical Roots
Photograph by Tiffany Nolasco and Mustafa Hooten for Crown Royal Izaya Hill and family members shared heartfelt moments, emphasizing the importance of heritage and musical influence in Lauryn Hill’s life.
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Celebrating Artistic Collaborations
Photograph by Tiffany Nolasco and Mustafa Hooten for Crown Royal Rapsody and Rah Digga highlighted the ongoing influence of Lauryn Hill’s work, inspiring a new generation of artists.
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Honoring the Next Generation
Photograph by Tiffany Nolasco and Mustafa Hooten for Crown Royal Emerging artists like Tanikka Charrare and her collaborators paid tribute through performances, showcasing the enduring legacy of Lauryn Hill’s artistry.
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Community and Artistic Inspiration
Photograph by Tiffany Nolasco and Mustafa Hooten for Crown Royal Joseph Diaz and fellow creatives contributed to the vibrant celebration, emphasizing the collective spirit of artistic community.
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Celebrating Musical Heritage
Photograph by Tiffany Nolasco and Mustafa Hooten for Crown Royal Natasha Diggs, a renowned DJ and singer, added her voice to the night’s festivities, honoring Lauryn Hill’s influence on music and culture.
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Artistic Expression and Personal Tributes
Photograph by Tiffany Nolasco and Mustafa Hooten for Crown Royal Rah Digga’s presence underscored the deep respect and admiration held for Lauryn Hill’s groundbreaking contributions to hip-hop and soul.
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Honoring the Artistic Spirit
Photograph by Tiffany Nolasco and Mustafa Hooten for Crown Royal Stylist Raheem Robinson and vocalist Tara Harrison contributed to the night’s creative energy, celebrating Lauryn Hill’s enduring influence.
