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Bolton began recording in 1975 at The Church Studio in Tulsa, Oklahoma. This first album was self-titled using his original family name of Bolotin. 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 SabbathBolton later stated this was untrue, saying "That rumor about me auditioning for Black Sabbath was only a rumor, I don't know how on earth it started."
After anglicizing his family name to Bolton, he gained his first major hit as a songwriter, co-writing "How Am I Supposed to Live Without You" for Laura Branigan, previously best known for singing the pop hit "Gloria". Narrowly missing the Top 10 on the US pop chart, Branigan took the song to number one on the Adult Contemporary chart for three weeks in 1983. The two sought to work with each other again, and their next collaboration was when Bolton co-wrote "I Found Someone" for Branigan in 1985. Her version was only a minor hit, but two years later, Cher resurrected the song, and with it her own singing career. Bolton co-wrote several other songs for both singers. Bolton recorded his own rendition of "How Am I Supposed to Live Without You" in 1988, which reached number one on the Hot 100.
Bolton at the 1990 Grammy Awards
Bolton achieved his greatest success in the late 1980s and early 1990s as a singer on the adult contemporary/easy listening charts. One of his first major hits was his 1987 interpretation of the Otis Redding classic "(Sittin' On) the Dock of the Bay". Redding's widow, Zelma Redding, said she was so moved by Bolton's performance "that it brought tears to my eyes. It reminded me so much of my husband that I know if he heard it, he would feel the same." Always interested in soul and Motown classics, Bolton's success with that song encouraged him to tackle the standard "Georgia on My Mind", with which he had another hit. In 1991, Bolton released the album Time, Love & Tenderness which featured his Grammy Award-winning cover version of "When a Man Loves a Woman".
As a singer, he has performed with other artists such as: Lucia Aliberti, Patti LaBelle, José Carreras, Tony Cetinski, Ray Charles, Celine Dion, Plácido Domingo, Renée Fleming, Wynonna Judd, BB King, The Lonely Island, Luciano Pavarotti, Percy Sledge, and Zucchero. As a songwriter, he has written and collaborated on several songs for other artists as well.
Bolton's last Top 40 single in the US in his own right was the 1997 hit "Go the Distance" (featured in the Disney animated motion picture Hercules), which peaked at No. 1 on the US adult contemporary chart. He hired conductor Larry Baird (orchestral musical director/conductor/arranger for The Moody Blues, Three Dog Night, Al Jarreau, etc.) for his 2001 tour.
In 2006, Bolton and Nicollette Sheridan (his fiancée at the time) sang a duet, "The Second Time Around", for the album Bolton Swings Sinatra. In March 2007, Bolton toured South Africa for the first time. He was the headline act at Jacaranda 94.2 FM's two-day concert.
For Over the Rainbow, an album which was recorded in five days, Bolton recorded the song "New York, New York", which was also on his Bolton Swings Sinatra album. This was for an episode of the TV series, Challenge Anneka. The proceeds from the album went to children's hospices across the UK.
Bolton performed a duet entitled "Il Mio Amico" with the Italian singer Anna Tatangelo at the Sanremo Music Festival 2008. The song was originally sung by Tatangelo alone, but the duet version contained English lyrics as well.
Bolton's album Only a Woman Like You was released in 2001. The title song was co-written by Shania Twain. Bolton released his album One World One Love in the UK on September 21, 2009. The first single, "Just One Love", was released one week earlier.