The iconic Cher can get away with almost anything. When she was a 38-year-old lady, she got away with dating a 22-year-old young man by the name of Tom Cruise. Now, we aren’t really sure what they mean when they say “get away with” in this context. It’s not like people (let alone people in Hollywood) get punished for a relationship with an age gap.
He was just taking his first footsteps in the Hollywood world, while she had already built her reputation as a successful singer. The two dated for a while, not turning their story into something great. They were busier smiling to the cameras than actually trying to make something work.
Corey Feldman and Drew Barrymore
The child stars of the 1980s were very different than the ones we see today. Back then, if you appeared in one movie, you probably appeared in them all. During his teens, Corey Feldman starred in "Friday the 13th", "Gremlins," "The Goonies," and the all-time classic, "Stand by Me."
In 1989, Feldman dated Drew Barrymore, also known as a child star of those days. It's actually kind of sweet when you think about it — they were probably the only people who could fully understand each other. The two came together as an item to the Oscars that very same year.
Kate Moss and Johnny Depp
Johnny Depp and Kate Moss were quite an item for a hot minute. And by hit minute we mean about four years, between 1994 to 1998. In 2007, Johnny Depp was interviewed speaking fondly about Kate Moss, which would have made you think Moss and Depp had it going really well at the time.
Well, the truth is that it wasn't all that good. Their relationship came after Depp's love story with Winona Ryder, which became a huge story within the Hollywood tales and lasted for just over three years. All parties involved went on to have other high-profile relationships.
Gary Oldman and Uma Thurman
Uma Thurman is one you just gotta love. And Gary Oldman thought that, too, back in the 1990s. Oldman was Thurman's first true love, as she once said in an interview. She said she was a young and inexperienced woman involved with a man twelve years her senior.
She also said that it isn't a surprise that their relationship ended when it did — less than two years after they tied the knot. Uma even took it a step further by adding that this was the mistake of her life. He was 12 years older than her, and what was done has been done.
Madonna and Vanilla Ice
The queen of pop dating the king of ice cream. What a strange couple they were. There was a slight age gap between the two, and according to Vanilla's story, she taught him many things he didn't know about relationships.
They dated for just under a year and broke up because Vanilla Ice didn't approve of the book she released at the time, which exposed him in a disrespectful way. Now, we ask you, Mr. Vanilla, it is known that the queen says whatever is on her mind, anywhere, anytime, and about anyone. What exactly did you expect when you started to date her?