5. “Iron Man 3” (2013)
Of course, this is a Christmas movie. Look at who made it. Director and co-writer Shane Black, who’d previously collaborated with Robert Downey Jr. on 2005’s “Kiss Kiss Bang Bang,” another ironic yuletide classic, took over for “Iron Man” and “Iron Man 2” director Jon Favreau, reminding audiences that Tony Stark will always be the most beloved of the Avengers. The reason, obviously, is Downey, who here gets to portray the irreverent tech genius/playboy as a more haunted individual, facing off with a frightening terrorist who goes by The Mandarin (Ben Kingsley). Subverting aspects of Iron Man’s comic book history while delivering a surlier, more soulful superhero movie, Black brought the same witty approach to action films that he incorporated into his “Lethal Weapon” script so long ago. As for Downey, he got a more epic farewell in “Avengers: Endgame,” but “Iron Man 3” might be his best Stark performance.
4. “Mission: Impossible III” (2006)
The third chapter in the “Mission: Impossible” saga now occupies a strange corner in the franchise. At the time, it was seen as a strategic readjustment after the overblown “Mission: Impossible 2,” with J.J. Abrams (the TV guy behind “Felicity,” “Alias” and “Lost”) making his feature directorial debut. But with apologies to those who adore the Brian De Palma-helmed original, “Mission: Impossible III” is my favorite of the first three, presenting Tom Cruise’s Ethan Hunt with one of his greatest foes, Philip Seymour Hoffman’s stone-cold arms dealer Owen Davian. This was a period when people wondered if Cruise was “over”—he had appeared on “The Oprah Winfrey Show” a year earlier, resulting in the couch jump heard ‘round the world—and “III” wasn’t the blockbuster Paramount had hoped it would be. But although the subsequent sequels are superior, this 2006 film is a fleet action-thriller that pares away some of the gaudy spectacle for a gripping, James Bond-ian adventure.
3. “Iron Man” (2008)
It was striking to see Christopher Nolan and Robert Downey Jr. together at the Oscars this year, both receiving kudos for their work on “Oppenheimer.” Sixteen years earlier, they had rocked the industry in a completely different way. In July 2008, “The Dark Knight” profoundly changed how Hollywood approached superhero films—meanwhile, two months earlier, “Iron Man” announced there was a new sheriff in town, the colossus known as Marvel. Director Jon Favreau had made the appealing Christmas film “Elf,” and Downey had once been a beloved actor, although his addiction issues had, for a time, rendered him practically unemployable. Unlikely as it might have seemed back then, the two of them created a template for Marvel films that would soon become the envy of the industry. “The Dark Knight” remains the better movie, but “Iron Man” gave the world Downey’s impossibly charming, amusingly arrogant Tony Stark, whose world of fast cars, cool gadgets, and expensive digs could rival Bruce Wayne’s—who seemed way more troubled than this grinning smartass. Everything Marvel would achieve over the next 11 years of global box office dominance springs from here.