Patrick Dempsey's biggest moments over the years

By Jessica Wedemeyer 8:43am PDT, Aug 10, 2017

It's been 30 years since "Can't Buy Me Love" debuted in theaters on Aug. 14, 1987. Patrick Dempsey starred in the teen rom-com as a nerdy high school kid who pays a popular cheerleader to pretend to be his girlfriend. In honor of the movie's big anniversary, Wonderwall.com is taking a look back at the former teen idol and his biggest moments over the years. Keep reading for Patrick's greatest hits…

Patrick Dempsey made his acting debut in 1985's "Heaven Help Us." He portrayed Corbett in the dramedy, which centered around a group of misfits at a Catholic prep school in the '60s. Malcolm Danare, Andrew McCarthy, Kevin Dillon, Stephen Geoffreys and Jay Patterson also starred in the film.

Patrick Dempsey made his television debut in 1986 on "Fast Times," the CBS TV show based on the movie "Fast Times at Ridgemont High." He portrayed Mike Damone alongside Wallace Langham and Courtney Thorne-Smith on the short-lived sitcom, which lasted just seven episodes.

Patrick Dempsey headlined a film for the first time with 1986's "Meatballs III: Summer Job." He starred as Rudy, a nerdy teen who's visited by the ghost of porn star (Sally Kellerman) whose mission is to help him lose his virginity before she can cross over to the afterlife.

Patrick Dempsey married his first wife, acting coach-manager Rochelle "Rocky" Parker, in 1987 when he was just 21 years old and she was 47. The duo, who are pictured together during the Second Writers Guild of America Awards in 1990, reportedly split in 1993 and divorced in 1994. (Rocky died of throat and lung cancer in 2014.)

Patrick Dempsey starred opposite Amanda Peterson in 1987's "Can't Buy Me Love." His role in the teen rom-com helped make him one of the biggest geek-chic heartthrobs of the decade of decadence. He went on to star in "Some Girls," "Loverboy" and "Happy Together" before the '80s came to an end.

In 1994, Patrick Dempsey made an appointment to get his hair cut at a salon in Los Angeles. He became friends with stylist Jillian Fink, who'd go on to cut his hair for the next three years until he finalized his divorce from first wife Rocky Parker and they finally became a couple. The duo tied the knot in 1999.

Patrick Dempsey's career cooled during the '90s, but he scored an Emmy nomination in 2001 for his work on "Once and Again." (He had a four-episode stint on the ABC family drama as Aaron Brooks between 2000 and 2002.) His wife, Jillian Fink, accompanied him to the Creative Arts Emmys in Los Angeles that year, where he lost the award for Outstanding Guest Actor in a Drama Series to Michael Emerson. (Patrick also had a three-episode stint on "Will & Grace" around this time.)

Patrick Dempsey made his major rom-com comeback with 2002's "Sweet Home Alabama." He portrayed one corner of a love triangle — the mayor of New York City's wealthy son — alongside Reese Witherspoon and Josh Lucas.

Patrick Dempsey and wife Jillian Fink welcomed their first child, daughter Talula Fyfe, in 2002. (He was photographed carrying his little girl during the 32nd Annual Toyota Grand Prix of Long Beach in 2006.)

Patrick Dempsey portrayed Ben Weissman opposite Hilary Swank's Alice Paul on the 2004 HBO suffragette drama "Iron Jawed Angels." The made-for-TV movie earned five Emmy and three Golden Globe nominations.

"Grey's Anatomy" debuted on ABC on March 27, 2005. Patrick Dempsey starred as Dr. Derek "McDreamy" Shepherd for 11 seasons on the medical drama until his character died in May 2015. He won three People's Choice Awards and earned a SAG Award nomination for his work on the show, which also helped him score lead roles in rom-coms like 2007's "Enchanted," 2008's "Made of Honor" and 2010's "Valentine's Day."

Patrick Dempsey earned his first Golden Globe nomination in 2006 for his work on "Grey's Anatomy." (His wife, Jillian Fink, accompanied him to the award show in Beverly Hills that year.) He earned his second nomination for best actor in a TV drama the following year.

Patrick Dempsey and wife Jillian Fink welcomed twin sons, Sullivan Patrick and Darby Galen, in 2007. (The actor was photographed with his boys during the Monster Energy Supercross in Anaheim, California, in 2016.)

In 2008, Patrick Dempsey launched the Dempsey Center in Lewiston, Maine. According to The Hollywood Reporter, the center works closely with oncologists at the Central Maine Medical Center and "offers wellness services, support and education to anyone impacted by cancer." The actor was moved to open the center by his mother's prolonged battle with ovarian cancer. (She died in March 2014 after a 17-year fight against the disease.) In 2009, Patrick launched the Dempsey Challenge, a charity run/walk or cycling ride to raise funds for the center.

Patrick Dempsey starred as a math whiz caught in the middle of a bank heist in the forgettable 2011 crime-comedy "Flypaper," which performed poorly with critics and at the box office. It's notable for only one reason: It was the first time the handsome star produced a film.

In 2012, Patrick Dempsey made his major blockbuster debut as the villainous Dylan Gould, the boss of Rosie Huntington-Whiteley's Carly, in "Transformers: Dark of the Moon." On the one hand, he earned a Razzie Award nomination in the worst supporting actor category for his performance in the sci-fi action flick. On the other, the third installment in the "Transformers" franchise made more money at the global box office than any other film he's appeared in, and by leaps and bounds — it made more than a billion dollars in a month! By comparison, Patrick's second-highest-earning movie, "Enchanted," made more than $300 million at the global box office.

In 2013, Patrick Dempsey starred on a four-episode Velocity channel docu-series about his life as a racecar driver and attempt to compete in France's 24 Hours of Le Mans endurance race, "Patrick Dempsey: Racing Le Mans," which he also executive produced. ("I just love it," the multi-talented star once told People magazine of racing. "It's really stimulating both physically and mentally.")

Patrick Dempsey and wife Jillian Fink recommitted to their marriage in late 2015 after the hair and makeup artist filed for divorce earlier in the year. They made their first red carpet appearance following the hiccup in their relationship (along with their three children) at the London premiere of "Bridget Jones's baby" on Sept. 5, 2016.

Patrick Dempsey proved there's life after "Grey's Anatomy" with 2016's "Bridget Jones's Baby," his first acting gig following the death of Dr. Derek Shepherd. He starred as Bridget's new suitor, Jack Qwant, in the romantic comedy.