Paul Newman/Robert Redford
Shared Filmography: “Butch Cassidy & The Sundance Kid” (1969), “The Sting” (1973)
Paul Newman and Robert Redford have a much smaller number of films together than most actors on this list, but that they were the first who came to mind speaks to the iconic nature of their team-up. It’s partly because the two are probably the best-looking men to ever grace the silver screen, so putting them together was always going to be a pleasure. And it’s partly that their two films together are both classics to one degree or another. “Butch Cassidy” is the best of the two: a gloriously entertaining, whip-smart Western about the legendary outlaws benefitting enormously from the warmth and humor brought by the pair, with their real-life friendship being positively palpable. “The Sting,” which reunited them with ‘Butch’ director George Roy Hill, is a little thinner (though unlike the earlier film, it won the Academy Award for Best Picture), but is still enormously enjoyable, and perhaps plays better into their age difference, the older/younger brother feel they had in real life. The pair stayed lifelong friends, and did nearly make a third film, “A Walk In The Woods,” which Redford finally made this year. Nick Nolte takes the role once intended for Newman, and while we love Nolte as much as Newman, it’s hard to think about what could have been.
Best Film Together: “Butch Cassidy & The Sundance Kid”
Typical Quote:
Butch (Newman): “Listen I don’t mean to be a sore loser, but when it’s done, if I’m dead, kill him.”
Sundance (Redford): “Love to.”
Ben Stiller/Owen Wilson
Shared Filmography: “The Cable Guy” (1996), “Permanent Midnight” (1998), “Meet The Parents” (2000), “Zoolander” (2001), “The Royal Tenenbaums” (2001), “Starsky & Hutch” (2004), “Meet The Fockers” (2004), “Night At The Museum” (2006), “Night At The Museum: Battle Of The Smithsonian” (2009), “Little Fockers” (2010), “Night At The Museum: Secret Of The Tomb” (2010) “Zoolander 2” (2016)
Given the incestuous nature of the modern comedy scene, with everybody cropping up for cameos in each other’s movies, it’s easy to overlook that Ben Stiller and Owen Wilson have appeared in eleven movies together (with a twelfth on the way). Admittedly, they haven’t always shared screen time, and six of those movies come from two not-so-great comedy trilogies, “Meet The Parents” and “Night At The Museum,” but their co-starring roles have been memorable enough to make them one of the bigger present-day comedy teams. Soon after his breakout in “Bottle Rocket,” Wilson had a small role in Stiller’s second movie as director, the dark Jim Carrey comedy “The Cable Guy,” then paired with him on addiction drama “Permanent Midnight,” but the film that really launched them as co-stars was Stiller’s absurdist comedy “Zoolander,” with the actors playing moronic male models. They’re a classic odd couple: Stiller the neurotic, uptight Jewish guy, Wilson the impossibly laidback WASP, but as “Zoolander” and cop parody “Starsky & Hutch” demonstrated, their personas could stretch to far more than just that, even while they always prove perfectly complementary. Recent collaborations have been limited to Wilson’s cameos (mostly as a tiny cowboy) in Stiller’s franchise movies, but with “Zoolander 2” on the way, it’ll be good to see them sharing screen space again.
Best Film Together: It’s not exactly a Stiller/Wilson vehicle, but “The Royal Tenenbaums” is certainly the best movie to feature both actors (Wilson also wrote it).
Typical Quote:
Starsky (Stiller): “It’s 10 o’clock, you’re late; I’ve been here since 8.”
Hutch (Wilson): “8’o clock? I didn’t even know this place opened at 8.”
Starsky: Well, don’t sweat it, ‘cause ya know what? Crime called in sick, it’s gonna get a late start too.”
Kirk Douglas/Burt Lancaster
Shared Filmography: “I Walk Alone” (1948), “Gunfight At The O.K. Corral” (1957), “The Devil’s Disciple” (1959), “The List Of Adrian Messenger” (1963), “Seven Days In May” (1964), “Victory At Entebbe” (1976), “Tough Guys” (1986)
Most big-screen cinematic pairings have an established brand that goes with them, and mostly on the comedy side: you expect fast-talking fireworks with Loy and Powell, or lowbrow slapstick with James and Sandler. Not so Kirk Douglas and Burt Lancaster. Two of Hollywood’s great leading men starred in seven (well, mostly six, but we’ll come to that…) films across nearly forty years, from film noir to period drama to Western to conspiracy thriller to ’80s actioner, a list all the more atypical because they were never particularly close friends, unlike many of the actors in this list. Film noir “I Walk Alone” was their first project, with Lancaster top-billed and Douglas as his former Prohibition frenemy, a hierarchy that continued across almost all their appearances together. They played Wyatt Earp and Doc Holliday at “Gunfight at the OK Corral,” riffed on George Bernard Shaw in “The Devil’s Disciple,” and battled over the fate of the country in “Seven Days In May” before reteaming for old-timers-bank-robbers action-comedy “Tough Guys,” co-starring Dana Carvey, of all people. It’s hard to pin down their chemistry, given their roles were so different, but their fierce, burning screen presences were certainly complementary and are a pleasure to watch whether they played fierce adversaries or old pals. And that seventh film? John Huston’s murder-mystery “The List Of Adrian Messenger,” an odd movie sold on the premise that a number of big stars were ‘disguised’ in the movie, revealing their identities in the credits: actually, their roles were played by someone else, and Lancaster only filmed his single credits shot.
Best Film Together: ‘O.K. Corral’ is very good, but their best work together was John Frankenheimer’s “Seven Days In May,” a crackling conspiracy thriller with Douglas out to foil an attempted coup by Lancaster’s General.
Typical Quote:
Wyatt Earp: “We’d like you to come to the wedding, Doc – if it doesn’t interfere with your poker.”
Doc Holliday: “I’m not good at weddings – only funerals. Deal me out.”
Katharine Hepburn/Spencer Tracy
Shared Filmography: “Woman of the Year” (1942), “Keeper of the Flame” (1942), “Without Love” (1945), “The Sea of Grass” (1947), “State of the Union” (1948), “Adam’s Rib” (1949), “Pat and Mike” (1952), “Desk Set” (1957), “Guess Who’s Coming To Dinner” (1967)
The mythologized subjects of a 25-year-long off-screen love affair (Tracy never divorced his wife and even though Hepburn nursed him through his final illness, she did not attend his funeral out of respect for his family), it’s an opposites-attracting narrative that colors every one of Spencer Tracy and Katharine Hepburn’s nine onscreen collaborations. With most of the films enjoying a kind of battle-of-the-sexes vibe (“Guess Who’s Coming to Dinner” is maybe the only one where that dynamic takes a backseat to another issue; even Elia Kazan‘s unsatisfying “The Sea of Grass” is an attempt at a dramatic, rather than comedic, take on that territory), many can now feel dated. By their conclusions, usually the outspoken Hepburn has to be somewhat tamed into domesticity by Tracy’s plain-spoken masculinity. But the sizzle that endures is not in final morals, but in the crackle of the back-and-forth interactions in which they seem to be eternally playing out variations on the same theme: can’t live with ’em, can’t live without ’em. While so many other classic Hollywood pairings issued from a kind of synergy (Astaire/Rogers; Flynn/De Havilland), the ongoing onscreen friction between Tracy, ever the underplaying naturalist, and Hepburn, all clipped vowels and haughty angularity, gives these films a charge they retain even in more enlightened times.
Best Film Together: “Adam’s Rib”
Typical Quote: from “Adam’s Rib”
Amanda: There’s no difference between the sexes. Men, women, the same.
Adam: They are?
Amanda: Well, maybe there is a difference, but it’s a little difference.
Adam: Well, you know as the French say…
Amanda: What do they say?
Adam: Vive la difference!
