Gwyneth Paltrow at an event for Shakespeare in Love (1998)
Many critics think Cate Blanchett gave her best performance ever as Queen Elizabeth I in Elizabeth, but it was Gwyneth Paltrow who won Best Actress at the 1999 Oscars for her performance in Shakespeare in Love. The film's production company ran an ad campaign that argued Paltrow played multiple roles in the comedy since her character was an actress who disguised herself as a man so she could appear onstage. The Oscar voters were convinced.