The 90s were a decade that will forever be looked upon fondly when it comes to entertainment, as the period was one that is remembered as a renaissance and coming-out party for black creatives in television and film. While comedic sitcoms and films catering to the urban demographic often get a majority of the fanfare, it could be argued that dramatic shows and films of the romantic variety have gone down as some of the most pivotal, one of them being the 1998 flick How Stella Got Her Groove Back, a movie that inspired a generation of women to regroup and pursue their best life. Adapted from author Terry McMillan’s best-selling novel, How Stella Got Her Groove Back stars Angela Bassett as Stella Payne, a middle-aged single mother who is persuaded to take a break from her career as a successful stockbroker and go on a lavish vacation to Jamaica for some rest and relaxation. However, Stella is unexpectedly swept off of her feet by Winston Shakespeare (played by Taye Diggs), a man 20 years her junior who pursues Stella, resulting in a whirlwind romance that prompts Stella to reevaluate her life and her priorities.

Featuring a supporting cast that includes Whoopi Goldberg (as Delilah Abraham), Regina King (as Vanessa) and other star talent, How Stella Got Her Groove Back was a runaway success, grossing nearly $40 million worldwide at the box office, and has become a certified classic and one of the most beloved romantic dramas of the late 90s. The film itself has gone on to become a favorite among movie buffs in the black community, however, How Stella Got Her Groove Back was also accompanied by a stellar soundtrack that often gets overlooked when lists of the most memorable are compiled. Entirely produced by legendary production/songwriting duo Jimmy Jam and Terry Lewis, with additional contributions from Wyclef Jean, Jerry Duplessis and Salaam Remi, How Stella Got Her Groove Back‘s soundtrack played heavily to the film’s tropical setting, with a list of the biggest names in hip-hop and R&B joining forces with dancehall and reggae artists for a collection of tracks that speak to the B-Boy or the Islander in you.

With today marking 20 years since this film hit theaters, REVOLT TV decided to celebrate the occasion by highlighting five songs from the soundtrack.

5 | “Free Again,” Soul II Soul

“Well, memories they flood my mind,” Jazzie B drawls on the opening verse of “Free Again,” a mid-tempo selection from Soul II Soul that finds the group meshing their British and Caribbean roots. Produced by Jam and Lewis, “Free Again” is powered by lead singer Caron Wheeler, whose strong vocal performance makes this breezy composition one of the premier selections from the Stella soundtrack.

4 | “Make Me Sweat,” Big Pun ft. Beenie Man

Riding high off the success of his platinum-certified album Capital Punishment, Big Pun carried over the Caribbean vibes from standout tracks like “Caribbean Connection” onto this contribution to the Stella soundtrack. Titled “Make Me Sweat,” the ditty finds the Bronx bomber teaming up with Beenie Man and beckoning the ladies from the dancefloor into the bedroom on one of the island-tinged project’s more impressive offerings.

3 | “Escape to Jamiaca,” Lady Saw and Nadine Sutherland

Stella‘s soundtrack delivers one of its finer offerings with “Escape to Jamaica,” a pulsating ditty that finds Grammy Award-winning Lady Saw teaming up with fellow Jamaican vocalist Nadine Sutherland. Turning in a pair of patois-tinged stanzas and ad-libs amid Sutherland’s sultry vocals, the Queen of Dancehall leads the charge on “Escape to Jamaica,” a track inspired by Bassett’s character’s romantic getaway.

2 | “Mastablasta ’98,” Stevie Wonder ft. Wyclef Jean

One of the more intriguing collaborations on the Stella tracklist is “Mastablasta ’98,” which features musical icon Stevie Wonder crooning alongside versatile rapper-producer Wyclef Jean. Produced by Jean, Jerry Duplessis, and Jam and Lewis, “Mastablasta ’98” is powered by a sample of Donald Byrd’s “(Fallin’ Like) Dominoes,” thumping percussion and guitar riffs, resulting in a gritty cover of Stevie Wonder’s classic single from his 1980 album, Hotter Than July, and a track that ranks as one of the best on the soundtrack.

1 | “Luv Me, Luv Me,” Shaggy ft. Janet Jackson

Recorded as a single for the Stella soundtrack, “Luv Me, Luv Me” paired reggae rapper Shaggy with pop star Janet Jackson for a high-powered collaboration that was symbolic of the romantic, feel-good vibes that defined the actual film. Rapping “A who da man dat love to make you moist and wet / A who da man dat love to make you moan and sweat,” Shaggy turns in a charismatic performance over a sample of “Impeach The President” by The Honey Drippers, while Janet Jackson delivers the hook, which samples the chorus from Rose Royce’s 1977 cut “Ooh Boy.” Accompanied by a music video that included cameos from cast members Bassett, Diggs, Goldberg, and King, “Luv Me, Luv Me” was a moderate hit despite not being released commercially, peaking at No.75 on the Hot 100 based off airplay alone. However, despite the success of the song, personal and creative differences between Shaggy and Jackson would result in Jackson’s parent label Virgin not clearing her vocals from the original version of “Luv Me, Luv Me” to be used on his fifth studio album, Hot Shot, shrouding the song in controversy. Shaggy would ultimately record a new version of the song, replacing Jackson with singer Samantha Cole, but the original version of “Luv Me, Luv Me” remains the one that comes to mind when most listeners think about the song and is the crown jewel of How Stella Got Her Groove Back, one of the most unsung soundtracks of its era.

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