Collaboration

His most extensive collaborations are with Dionne Warwick, having produced events for over 20 years, co-written three books with her tilted, "Say A Little Prayer", "Little Man" and her autobiography, My Life, As I See It—and produced her 50th anniversary gala at Lincoln Center.^[7][8] He also wrote, produced, and co-directed the documentary Dionne Warwick: Don't Make Me Over. The film received a standing ovation at the Toronto International Film Festival and won first runner-up for the People's Choice Award for Documentaries,^[9][10] later also winning the Best Feature honor at the Gene Siskel Film Center's Black Harvest Film Festival,^[11] receiving Centerpiece Screening at DOC NYC,^[12] and landing the Audience Award at the 2021 Montclair Film Festival.^[13] In a positive review of the documentary, Victor Stiff of That Shelf wrote, "[Co-director David Heilbroner] and Wooley pack their film with everything you want from a musical documentary: fantastic music, a one-of-a-kind star, and deep-cut stories from family and friends. It's an inspiring tale of overcoming the odds, filled with beautiful music and prudent life lessons along the way."^[14] The documentary premiered on CNN on January 1, 2023, debuting at #1 among cable news viewers aged 25–54.^[15] As of July 2023, the documentary has a Rotten Tomatoes critic's rating of 91% and audience rating of 100%.^[16] After the broadcast, it was made available on HBO Max.^[17]

Other projects

Wooley's career has extended into the sports sector. In 1988 he rose to prominence as the only Black man in the country to be awarded exclusive paid-per-view and closed-circuit television broadcasting rights for several entire states to the Mike Tyson versus Michael Spinks "Once And For All" match – the largest fight in history at the time. The fight grossed over seventy million dollars.^[18] He was subsequently featured in the 2021 documentary series Mike Tyson: The Knockout. Wooley was also awarded exclusive paid-per-view and closed-circuit television broadcast rights for several states to other championship fights including, the 1991 match-up, George Foreman vs Evander Holyfield.^[19][20]

In 1993, Wooley had a vision to develop an area of Wilmington Delaware Christina Riverfront into a family style entertainment destination by building a movie theatre and restaurants then called, Riverview Plaza. Later that year, It became a close reality when, Enterprise Developers Corporation led by Wooley which included, Julius "Dr.J" Erving, and investment banker, Malcolm D. Pryor Sr., won Wilmington City Council's request for proposal (RFP), during Mayor, James H. Sills, Jr's administration.^[21][22][23]

Wooley was the sole producer who came up with the idea for "The Clash of the Legends," a paid-per view TV hoopfest of 1992, which pitted retired NBA basketball players Julius "Dr. J" Erving and Kareem Abdul-Jabbar against one another.^[24] Wooley described the event as a spiritual descendent of the one-on-one games played between neighborhood legends in his native Harlem.^[25] Proceeds from the event went to benefit the American Foundation for AIDS Research, as well as the Magic Johnson Foundation, a charity established by the retired Laker star to battle against the HIV virus.^[26]

In 2024, Wooley served as Vice Chair for amFar (American Foundation for Aids Research), which held their fundraising gala in Palm Beach, Florida. The non-profit organization honored award-winning singer Dionne Warwick for her work as a trailblazer in HIV/Aids activism. Barry Gibb of the Bee Gees presented the award to Warwick. Recording artist Sting was the featured performer. The event raised 4.1 million dollars.^[27][28][29]