Love Overboard, written by Calloway and recorded by Gladys Knight & the Pips, won a Grammy Award for Best R&B Performance by a Group or Duo with a Vocal.
[5] Music written and produced by Calloway has been sampled in recordings by such artists as Snoop Dogg, Warren G, Busta Rhymes, Eric B.
& Rakim, E-40, Doug E. Fresh, A Lighter Shade of Brown, Usher (musician), Young MC, Sugar Ray, and numerous others.
[11] His mother opened her first business, Larson's Flower Barn and Ice Cream Parlor, where Calloway and his brothers Greg and Vincent worked until its closure in 1970.
In 1975 Reggie and brothers Vincent and Gregory, along with friends John Jones and Ruben Jordan, formed the jazz-fusion group SunChild.
The band, consisting of Calloway, Belinda Lipscomb, Melvin Gentry, Kenneth Gant, Bill Simmons, Bo Watson, and Jeff Cooper, were all students at the university.
He studied hit songs on the radio, paying close attention to what DJs were spinning in the clubs and hosted listening parties for his family and friends at home.
[22] Calloway honed in on production skills by shadowing songwriter/producers Leon Sylvers III and Harvey Mason in the recording studio.
[31] Calloway provided vocals on Skip Martin's 2021 charity single, People Get Ready, along with artists Stevie Wonder, Ray Parker Jr., Taylor Dayne, and Howard Hewett, among others.
[32][33][34] Dick Griffey, the President and owner of SOLAR Records, who had signed Midnight Star, asked Calloway and the band if they knew of any other talented groups in the Ohio area.
Calloway and Midnight star had signed the music group, The Deele, to their production company Mid-Star (which included band members Kenny Babyface Edmunds and LA Reid).
In the early 1980s he also co-produced, Radio Activity by Royalcash and co-wrote and produced singles, Contagious and Never Too Late for The Whispers.
In 1985 he co-wrote the title track for Klymaxx's album Meeting in the Ladies Room and co-produced Hello Stranger for Carrie Lucas.
[37] In 1987 his song, Jump Start, recorded by Natalie Cole was said by the press to have literally "jump started" her music career[38] and Love Overboard, written by Calloway and recorded by Gladys Knight & the Pips, won a Grammy Award for Best R&B Performance by a Group or Duo with a Vocal as well as being listed as one of their Top 10 Hits.