7. Pretty Woman (1990)

Richard Gere and Julia Roberts in Pretty Woman (1990).
Before it’s dropped in the comments, we’ll say it here: “Big mistake! Big! Huge!”

Interestingly, Pretty Woman was originally conceived to be a cautionary tale about class and prostitution in Los Angeles, but was reworked into the big-budget romantic comedy we know it to be.

Starring Julia Roberts and Richard Gere, Pretty Woman brought us a number of iconic moments that remain relevant over three decades later. That said, its reputation as one of the greatest romantic comedies every made isn’t entirely earned. Widely cited as the film that catapulted the overrated actor Julia Roberts to stardom, Pretty Woman‘s story is built around some potentially dangerous messages.

The first is that it’s essentially Cinderella if Cinderella was a sex worker. That’s all well and good – no judgement here – but Roberts’ character is far more trusting than she should be, and Gere’s character presents as far less creepy than he should.

Add to this the fact that neither of the two leads deliver particularly good performances, and the result is one of the most overrated films of all time.