His signature song "My, My, My" has been included on numerous romantic compilations.

Gill's recording career began in 1983, at the age of 17, when his childhood friend, singer Stacy Lattisaw, convinced him to record a demo. This demo fell into the hands of the president of Atlantic Records, and his self-titled debut album was released shortly thereafter, featuring the minor hit, "Super Love". On this album, Gill played guitar, bass, bongos, and drums in addition to performing lead and background vocals. Gill then teamed up with Stacy for a duet album, which featured their first hit together, the title track, "Perfect Combination". A second album on Atlantic Records yielded the song "Half Crazy", which is still a fan favorite.

Gill began a new chapter in his career in 1987, when he was recruited by Michael Bivins to join New Edition to replace lead singer Ralph Tresvant, who was rumored at the time to be leaving to pursue a solo career. Gill became the only member of New Edition who was not from Boston.

With Gill, the oldest member, as one of the lead singers (along with Tresvant, who ended up staying with New Edition and delaying the launch of his solo career) on the album Heart Break, the group developed a more mature, adult sound, hitting the charts with songs such as "Can You Stand The Rain", "N.E. Heartbreak", "If It Isn't Love", and the Gill-led "Boys To Men".

Continuing his role as a romantic balladeer while emerging as a new jack swing star, he released a second self-titled album in 1990, which included the hits "My, My, My", "Rub You the Right Way", "Fairweather Friend", and "Wrap My Body Tight". In 1991, he was featured in Perri "Pebbles" Reid's hit single "Always" from the album of the same name, along with Pebbles' cousin, R&B singer, Cherrelle. The single made the R&B Top 20 shortly after its release.[

In 1993, Gill released another solo project, Provocative, which included the songs "Quiet Time to Play", "A Cute, Sweet, Love Addiction", and the gospel song, "I Know Where I Stand".

In 1996, Gill was reunited with New Edition, including Bobby Brown, as they recorded Home Again, an album noted for the singles "Hit Me Off" and "Still In Love".

In 1996, Gill also released Let's Get the Mood Right, which included the title song, "Love In an Elevator", and "Maybe" - which is considered by many to be one of his greatest vocal performances ever.

In 1997, he collaborated with Gerald Levert and Keith Sweat to form the supergroup LSG (Levert/Sweat/Gill), which yielded the multi- platinum debut album, Levert.Sweat.Gill, and a follow-up album in 2003 titled LSG2.

On September 27, 2008, he began touring with New Edition bandmates Ralph Tresvant and Bobby Brown in a new group named Heads of State.

In July 2010, Notifi Records, based out of St. Louis, MO, signed Gill to a recording contract. On October 11, 2011, Gill released his sixth studio album, Still Winning, which was his first album in 15 years. The first single off the album is titled "In the Mood

Gill has had over 80 television and film appearances as a singer and actor. He had a cameo role on the TV show Family Matters (TV series), and sang "You For Me" in the 2006 movie Madea's Family Reunion.

Gill starred in the 2009 stage play A Mother's Prayer, which also starred Robin Givens, Shirley Murdock, and Jermaine Crawford.

In 2008, Gill, as a member of New Edition, received the Golden Note Award at the ASCAP Rhythm & Soul Music Awards.

Although he has never been married, Gill is the father of a son, Isiah Gill, born in 2006, to a Washington DC journalist

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