21. Working Girl (1998)
An all-star assembly of talent on either side of the camera saw Working Girl’s corporate Cinderella story play incredibly well with both critics and audiences.
Carly Simon’s ‘Let the River Run’ scooped the Academy Award for Best Original Song, while stars Melanie Griffith, Sigourney Weaver and Joan Cusack were all nominated for their performances, along with further recognition in the Best Picture and Best Director categories.
Not a lot of rom-coms double as prestige awards-baiting dramas, but such a tightly-plotted and expertly crafted movie deserved all of the accolades that came its way.