By Neia Balao
9:00pm PST, Feb 27, 2023
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Who doesn't love Michael Bolton? After transitioning from heavy metal singer to pop-rock balladeer in the late '80s, the Grammy-winning artist known for his short-on-top, long-in-the-back hair and silky smooth voice quickly climbed the charts and rose to worldwide fame. To celebrate his 70th birthday on Feb. 26, 2023, we're taking a look back at the most nostalgia-inducing photos from early in the crooner's career…
On Jan. 15, 1990, Michael Bolton suited up — and puckered up his lips — for the Sixth Annual National Holiday Awards dinner honoring Martin Luther King Jr.
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Michael Bolton started dating actress Nicollette Sheridan in 1992 and they split five years later — only to reconcile in 2005, get engaged in 2006 and end their romance for good in 2008. The "When a Man Loves a Woman" crooner is seen here with the "Desperate Housewives" star during the Carousel of Hope Ball on Oct. 2, 1992.
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Michael Bolton had a brief romance with another "Desperate Housewives" actress too: Teri Hatcher. The pair, seen here at the premiere of "The Player" on April 3, 1992, began dating after Teri starred in his "Missing You Now" music video.
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Michael Bolton sure liked to fall for the women in his music videos! The Connecticut-born crooner fell for Ashley Judd after she appeared in his music video for "The Best of Love." He's seen here with the "Ruby in Paradise" actress, whom he dated for a little more than a year, during New York Fashion Week on Oct. 26, 1996.
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On Feb. 12, 2000, Michael Bolton was seen mingling with Donald Trump, the businessman's then-girlfriend Melania Knauss and future convicted sex trafficker Ghislaine Maxwell at Mar-a-Lago in Palm Beach, Florida.
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Why so pensive, Michael? Michael Bolton is seen here during an album signing in New York City on Sept. 7, 1990.
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On Jan. 12, 2001, Michael Bolton was photographed with "Baywatch" bombshell Pamela Anderson during Michael Jordan's celebrity golf invitational opening party at Atlantis in the Bahamas.
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Michael Bolton posed with Goldie Hawn during TNT's All Star Tribute to Joni Mitchell on April 6, 2000.
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Congrats, Michael! On Feb. 21, 1990, at the 32nd Annual Grammy Awards, Michael Bolton nabbed his first-ever Grammy Award! That evening, he took home the honor for best male pop vocal performance for "How Am I Supposed to Live Without You."
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Does it get more '90s than this? Michael Bolton is seen here with smooth jazz saxophonist Kenny G during the BMI Awards on May 21, 1991.
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Michael Bolton looked clean and cool in a white suit and tee for a performance on "The Tonight Show with Jay Leno" on Aug. 15, 1995.
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Michael Bolton and Nicollette Sheridan posed for a photo with a 23-year-old Mariah Carey during the 20th Annual American Music Awards on Jan. 25, 1993.
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We love a girl dad! Michael Bolton and daughter Holly Bolton, who was 15 at the time, enjoyed a father-daughter outing at the Kids for Kids Benefit for the Pediatric AIDS Foundation on April 18, 1993.
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How sweet are they?! Michael Bolton and then-girlfriend Nicollette Sheridan looked smitten with one another in matching looks (and hats!) when they attended Elvis: The Tribute in Memphis, Tennessee, on Oct. 8, 1994.
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Michael Bolton chatted with fellow music artist Paula Abdul during the Grammy Living Legends Gala on Nov. 21, 1989.
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He sure cleans up well! Michael Bolton posed for photos alongside a 28-year-old Gwyneth Paltrow during the Miramax Pre-Oscar Party on March 20, 1999.
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Michael Bolton… the skier? The "To Love Somebody" crooner enjoyed a day out on the mountain during VH1's Celebrity Ski in Squaw Valley, California, on March 12, 1992. We love the look, Michael!
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On June 22, 1997, Michael Bolton attended the premiere of Disney's "Hercules" in Los Angeles in an all-blue getup. He was more than just an audience member though — Michael actually sang the pop version of the song "Go the Distance" for the animated film!
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Michael Bolton and supermodel Naomi Campbell made the perfect pair when they posed for a photo together at a cocktail party at the Monte Carlo Music Awards in Monaco on March 5, 2002.
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Michael Bolton showed off his competitive side when he and the Bolton Bombers played a baseball game against David Foster and the Hollywood All Stars on July 19, 1992. Hmm… we wonder who won!
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We're not sure if we'd be as calm and collected as Michael Bolton if we were standing next to Brooke Shields! The "Said I Love You… But I Lied" singer is seen here with the model-actress during an Arista Records Grammy Awards pre-party on Feb. 19, 1991.
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If music didn't work out, maybe Michael Bolton would've considered a career in baseball! He's seen here during a game against Dees Demons in Los Angeles on Oct. 16, 1991.
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There's nothing more '90s than candid photos of celebrities at airports. Michael Bolton and then-girlfriend Nicollette Sheridan were spotted at LAX in Los Angeles on May 11, 1995.
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Michael Bolton showed off his airport style at Los Angeles International Airport on May 22, 1990. The "How Can We Be Lovers" pop singer opted for a leather jacket and blue jeans for his travel attire.
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During the premiere of HBO's "If These Walls Could Talk 2" on March 1, 2000, Michael Bolton was all smiles when he posed for a photo with Ellen DeGeneres and her then-love, late actress Anne Heche.
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On June 5, 1993, Michael Bolton was a guest at Mariah Carey and Tommy Mottola's New York City wedding. He was ready to take on the rainy weather with his umbrella!
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How spiffy is he?! Michael Bolton was spotted at the Nabisco Golf Championship at Mission Hills Country Club on March 21, 2000.
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Michael Bolton smiled big next to funnywoman Rosie O'Donnell during the first anniversary celebration of the now-defunct Rosie Magazine on April 15, 2002.
