Bolton performed in the hard rock and heavy metal music genres from the mid-1970s to the mid-1980s, both on his early solo albums and those he recorded as the frontman of the band Blackjack.

His early career also saw him as a successful songwriter, co-writing hits like "How Am I Supposed to Live Without You" for Laura Branigan, which he later recorded as a solo single.

Bolton achieved peak recognition as a pop ballad singer in the late 1980s and early 1990s with notable collaborations with songwriters like Diane Warren and Desmond Child.

During that time, he covered such songs as Otis Redding's "(Sittin' On) The Dock of the Bay" and Percy Sledge's "When a Man Loves a Woman".

In 2000, he faced a controversial legal battle with the Isley Brothers over plagiarism, which resulted in a substantial financial settlement.

His personal life includes a long-term relationship and broken engagement with actress Nicollette Sheridan and a 15-year marriage to Maureen McGuire, with whom he has three daughters.

[7] He has performed with artists including Lucia Aliberti, Patti LaBelle, José Carreras, Tony Cetinski, Ray Charles, Celine Dion, Plácido Domingo, Renée Fleming, Wynonna Judd, B.B.

With his parents' permission, he dropped out of high school and left home at age 15 to travel cross country along U.S. Route 66 and pursue music full-time.

Early in his musical career, he focused on hard rock, with his band Blackjack once opening for heavy metal artist Ozzy Osbourne on tour.

It was rumored that in 1983 Bolton auditioned for, but was denied, the lead vocalist position with Osbourne's former band, Black Sabbath.

"[16] Always interested in soul music and Motown classics, Bolton had a 1989 hit with a version of "Georgia on My Mind", a song associated with Ray Charles.

[26] In June 2011, Bolton collaborated with Indian musician A. R. Rahman for a song recorded for Gems – The Duets Collection.

[27] In 2013, Bolton released the album Ain't No Mountain High Enough: A Tribute to Hitsville U.S.A., which featured duets with Kelly Rowland, Melanie Fiona and Orianthi.

In March 2007, he toured South Africa for the first time, where he was the headline act at Jacaranda 94.2 FM's two-day concert.

He performed a duet entitled "Il Mio Amico" with the Italian singer Anna Tatangelo at the Sanremo Music Festival 2008.

[29] In May 2011, Bolton was featured as a guest vocalist in The Lonely Island's song "Jack Sparrow" on their Turtleneck & Chain album.

His performance with the comedic hip-hop trio focused on his (intentionally) off-topic chorus and miscommunication with the group, and the video featured him dressed in costumes as Jack Sparrow from Pirates of the Caribbean, Forrest Gump, Erin Brockovich, and Tony Montana from Scarface.

[36] In 2021, he guest-starred in season six of The Masked Singer where he sang Marvin Gaye & Tammi Terrell "Ain't No Mountain High Enough" with Faith Evans as "Skunk".

After he was eliminated on "DC Superheroes Night", he took the time to promote his upcoming album and did an encore by performing "How Am I Supposed to Live Without You".

The documentary features interviews with several business moguls, singers and other Detroit natives, including Christopher Ilitch, Jerry Bruckheimer, Francis Ford Coppola, Aretha Franklin, Smokey Robinson, and Alice Cooper.

He was raised in a liberal family, and describes his childhood home as having been decorated with both a Hanukkah menorah and a Christmas tree during the holidays.

[49][50] In January 2024, Bolton announced he had undergone emergency surgery for a brain tumor before the December 2023 holidays, and would take a break from touring for the rest of the year.

On July 25, 1993, Bolton played against Michael Jordan in a televised charity softball game at the Chicago White Sox stadium, Comiskey Park.

Bolton's team, The Bolton Bombers, composed of Bolton and his band, won the game 7–1 against Jordan's team, Jordan's Air Force, which was composed of celebrities including Magic Johnson, Chris Chelios, Ahmad Rashad, Evander Holyfield, Daniel Baldwin, William Baldwin, Mark Harmon, MC Hammer, Tom Selleck, and Stacey King, with Bo Jackson as coach.