Sherlock Holmes (2009)

Guy Ritchie’s Sherlock Holmes is a fun, quick-paced, and action-packed movie. Robert Downey Jr. provides the well-known detective with a fresh perspective in a way that only Robert Downey Jr. can, making it one of his best performances. Despite handling two significant series simultaneously—Iron Man and Sherlock Holmes—his performance is excellent. His performance on Sherlock won him a Golden Globe.

Chaplin (1992)

In Richard Attenborough’s 1992 biopic Chaplin, Robert Downey Jr. plays legendary actor and filmmaker Charlie Chaplin, giving Downey’s strongest performance of his career. Charlie Chaplin’s charm, humor, and melancholy are all expertly captured by him. Downey earned his first Academy Award nomination for the film

Less Than Zero (1987)

Less Than Zero, which is based on the same-titled book by Brett Easton Ellis, depicts three rich friends as they get separated after high school. Clay (Andrew McCarthy) finds his closest buddy Julian (Downey) in the grips of serious drug addiction when he returns home from college. Downey portrayed the drug-dependent Julian with a heartbreaking yet sympathetic performance. Robert Downey Jr. gave one of his greatest performances in the film Less Than Zero, which also served as the trigger for his successful career.

Tropic Thunder (2008)

Tropic Thunder was never intended to be offensive; rather, it was supposed to show how ignorant method actors are. As Australian actor Kirk Lazarus, who surgically dyes his skin to portray an African-American Vietnam Sargent, Robert Downey Jr. provides one of his funniest performances. For his efforts, Downey was nominated for an Oscar for Best Supporting Actor.