“Moulin Rouge!” (2001)
No one expected “Moulin Rouge!” to become the kind of phenomenon that it did. An operatic musical, shot in a hyperactive MTV style, using mash-ups of popular, anachronistic songs, from the guy who directed “Romeo & Juliet?” Really? But the film proved to be both a critical and commercial hit, prefiguring the revival of the genre, and picked up 8 Oscar nominations, including Best Picture, and landed on many “best of the decade lists” when the time came. While we’re not convinced as to how well the film has dated, it remains an impressive feat and, while Nicole Kidman got most of the critical plaudits, McGregor’s performance as romantic lead Christian is really what makes the film work. It’s a tricky one to pull off, a combination of romantic naivety, seductive charm, and some incredibly broad humor, but the actor manages it with aplomb; there are few actors that would have managed to play the part sincerely, without winking at the camera (and plenty of actors in the film do the latter), but McGregor has to play it straight, and smashes it. And his singing voice turned out to be genuinely impressive, particularly in his rendition of Elton John‘s “Your Song,” paving the way to a starring role on stage in “Guys & Dolls.”
“Down With Love” (2003)
McGregor’s never quite been praised for his comic chops, but he’s got them in spades (every performance on this list shares a certain wit to them that few actors would have brought), and they received their best showcase in Peyton Reed‘s terminally underrated 2003 romantic comedy “Down With Love.” A souffle-light tribute to the Doris Day/Rock Hudson comedies of the 50s and 60s, McGregor plays the excellently-named Catcher Block, a womanizing journalist who attempts to seduce writer Barbara Novak, a writer whose new book has caused a feminist storm in 1960s New York. Reed, who followed it up with the disappointing “The Break Up” and “Yes Man,” nails the style, immaculately pastiching the Day/Hudson originals, and his cast is more than game: McGregor might be more Cary Grant than Rock Hudson, but he’s enormous fun, and has oodles of chemistry with co-star Renee Zellweger. The film tanked hard on release, crushed when released head-to-head with “The Matrix Reloaded,” but it’s become something of a cult classic since, and with good reason.