Things That Actually Existed: ‘Michael Bolton’s Winning Softball’

“I’ll be honest with you, I love his music. I do. I’m a Michael Bolton fan. For my money, I don’t know if it gets any better than when he sings ‘When a Man Loves a Woman’.” – Bob Slydell

Between that quote from Office Space and the infectious “Jack Sparrow” ballad collaboration with Andy Samberg and Lonely Island, crooner Michael Bolton’s legacy has been tarnished over the past decade and molded into some sort of a sick joke. The truth is that before this generation’s pop music corroded our airwaves and Pandora stations with Biebers and Gagas, Bolton was the powerful voice of adult contemporary love rock.

Bolton set the loins of many a future cougar ablaze with his incredible anthems like “How Am I Supposed to Live Without You” (later famously covered by AC Slater and Jessie Spano as the soundtrack of the monumental Zack and Kelly breakup) and “I Said I Loved You (But I Lied)”, which when taken for just the title sounds like the meanest song ever. But what few people know or recall is that when Bolton wasn’t rocking the most romantic receding mullet of the 80s and 90s, he was actually tearing up softball fields from coast-to-coast.

While his softball prowess came to the nation’s attention as part of MTV’s iconic (and sorely missed) Rock N Jock series, it culminated with the incredible VHS instruction video – Michael Bolton’s Winning Softball. Eat your heart out, Tom Emanski.

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