Brad Pitt and Christina Applegate: The actors dated briefly in the late '80s. Apparently, Applegate ditched Pitt during the MTV Movie Awards for another actor whose identity she wouldn't reveal, even when pressed by Andy Cohen on "Watch What Happens Live" two decades later.
Tommy Lee and Heather Locklear: The 24-year-old "Dynasty" actress shocked everyone when she married the 23-year-old Motley Crue drummer in 1986. She famously quipped: "Tommy doesn't worship the devil; he worships me." The couple split in 1994 amid numerous allegations that Lee also worshipped groupies while on tour.
Drew Barrymore and Corey Feldman: According to Feldman's memoir, "Coreyography," the two child stars had their first date arranged by Barrymore's mother when he was 14 and she was 10. They later dated for real in 1989 while she was in her mid-teens. Feldman wrote in his memoir that he was heavily into to drugs at the time and Barrymore was trying to stay sober after multiple trips to rehab.
Kim Basinger and Prince: The actress and the singer dated for a short time in 1989. In a 2015 interview with The Daily Beast, Basinger had this to say about The Purple One: "He's a brilliant talent. ... I don't really have boundaries, so I enjoyed that time of my life. It was a really special moment in time, and I have great memories."
Matthew Broderick and Helen Hunt: The actors dated briefly in 1987 and remained close friends after their breakup. They even starred together in 2007's "Then She Found Me."
Tom Cruise and Cher: Cher told Bravo's Andy Cohen in 2013 that Cruise was in her top 5 list of lovers. The two stars, with a 16-year age gap, had a fling in the mid-'80s after Cruise was coming off his giant success with "Risky Business." She told Oprah Winfrey in 2008 that she had been "crazy" for the actor.
Kelly Preston and George Clooney: Before she married John Travolta, Preston dated heartthrob Clooney from 1987-89. The pair of actors even lived together with their potbellied pig, Max, whom Clooney continued to raise after their breakup.
Paula Abdul and Arsenio Hall: These two were hot and heavy in 1989, but the relationship soon fizzled. There were talks 20 years later that they had rekindled their flame, but those turned out to be just rumors.
Emilio Estevez and Demi Moore: Before Bruce Willis and way before Ashton Kutcher, Moore was engaged to Estevez. The two met on the set of "St. Elmo's Fire" in 1984, became engaged a year later and broke up in 1987.
Sarah Jessica Parker and Robert Downey Jr.: Before "Sex and the City" and her marriage to Matthew Broderick, Parker dated Downey from 1984-1991. He told Howard Stern in 2015 that his struggles with addiction played a major role in their breakup, and he said he recently had a "friendly reunion" with Parker that allowed him to gain closure.
Sylvester Stallone and Brigitte Nielsen: The pair met in 1985 and were married within a few months, when Nielsen was 22 and Stallone was 39. They had just starred in "Rocky IV" together. The two were married for 19 months before they divorced in 1987.