In the mid-1980s, Michael Bolton, then known as Michael Bolotin, was at a crossroads. After years of performing hard rock with his band Blackjack, he made a daring pivot into the world of pop ballads. This risky transition led him to a remarkable peak in the late 1980s and early 1990s, culminating in the compilation album Greatest Hits: 1985 - 1995. It showcases a decade's worth of emotional anthems, each a testament to his vocal prowess and heartfelt songwriting.

Among the standout tracks, "How Am I Supposed to Live Without You" holds a special place. Co-written by Bolton and Doug James and first recorded by Laura Branigan in 1983, it became an emblem of Bolton's journey when his own 1989 recording topped the Hot 100 in early 1990. This song encapsulates the essence of his new direction, blending powerful lyrics with a soaring vocal performance that became his signature. Another notable track, "When a Man Loves a Woman," is a soulful cover of Percy Sledge's song. Bolton's rendition transforms it into a passionate ballad that resonates deeply with listeners, showcasing his ability to infuse new life into cherished music.

The album also features "Time, Love and Tenderness," the title track of his 1991 album, which captures the themes of love and longing, subjects that Bolton mastered during this period. It highlights his evolution as a singer and songwriter, drawing on the emotional depth that propelled him into the limelight. Through collaborations with prolific songwriters like Diane Warren, Bolton developed a sound that carved a niche in the adult contemporary genre, despite facing critiques of being derivative.

As Bolton continued to grow, he not only garnered commercial success but also became a philanthropist, founding The Michael Bolton Charities. His journey reflects resilience and adaptability, traits that resonate in his music. From his hard rock beginnings to becoming a pop ballad powerhouse, Greatest Hits: 1985 - 1995 is a celebration of his artistic evolution and enduring appeal.

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