Jack Lemmon
Total Nominations: Eight. One in supporting, for 1955’s “Mister Roberts,” and seven in lead for “Some Like It Hot” (1959), “The Apartment” (1960), “Days Of Wine And Roses” (1962), “Save The Tiger” (1973), “The China Syndrome” (1979), “Tribute” (1980) and “Missing” (1982).
The Films He Won For: When you think of Jack Lemmon, you think of his glorious collaborations with Billy Wilder, or his moving work later in his career as he became an elder statesman and moved into more serious, dramatic fare. You probably don’t think of “Mister Roberts” or “Save The Tiger,” and yet those were the films that Lemmon won Best Supporting Actor and Best Actor for, respectively (making him the first actor to do the double). The former is a troubled adaptation of a stage hit (John Ford was fired after punching star Henry Fonda in the jaw) that gives the young Lemmon a good showcase, but is otherwise fairly minor when put against some of his better career works. The latter is an affecting though rather loose and overstuffed performance showcase—a very atypical Oscar winner—that helped Lemmon shift into more middle-aged, dramatic roles. It’s a very good performance in a film that’s maybe unjustly neglected these days, but Lemmon probably should have picked up a Best Actor trophy long before it.
The Films He Should Have Won For: Given the Academy’s usual distaste for comedy, it’s remarkable that Lemmon was even nominated for Billy Wilder‘s “Some Like It Hot” and “The Apartment.” But given that they’re two of the greatest comedic performances in American cinema, was it too much to hope that he’d win for either of them? Impressively, the two turns, delivered in back-to-back years, are very different—as Jerry in “Some Like It Hot,” he’s a comic whirlwind, brilliantly and accidentally getting swept up in his drag disguise, while he’s positively heartbreaking in “The Apartment” even as he makes you laugh ’til you’re snorting out of your nose. He was beaten by Charlton Heston in “Ben Hur” and Burt Lancaster in “Elmer Gantry,” respectively, but we know which way we’d have voted in both cases.
Shirley MacLaine
Total Nominations: Six—five leading actress nominations, for “Some Came Running” (1958), “The Apartment” (1960), “Irma La Douce” (1963), “The Turning Point” (1977) and “Terms Of Endearment” (1983), plus a Documentary Feature nod in 1976 for “The Other Half Of The Sky: A China Memoir.”
The Film She Won For: “Terms Of Endearment,” James L. Brooks‘ comedy-drama that proved to be an unexpected Oscar juggernaut, picking up eleven nominations and winning five, including Best Picture and acting prizes for MacLaine and co-star Jack Nicholson. The film is a fairly superior example of an unfashionable genre, and probably ranks in the upper tier of Brooks’ spotty filmography (though “Broadcast News” obviously takes the top slot). MacLaine gets a lot to chew on, and satisfyingly underplays the material even when Brooks tips into sentiment, which is quite often. But the power of the film and the performance has been somewhat lessened over time by its many imitators and competitors (plus its unwelcome 1996 sequel “The Evening Star“). But ultimately, in retrospect, it doesn’t much stand up among even MacLaine’s subsequent work—her turns in “Postcards From The Edge,” “Bernie” or even the undervalued “In Her Shoes” are eminently more nominatable. Not to mention…
The Film She Should Have Won For: “The Apartment.” Billy Wilder‘s picture is credited by some these days as inventing the manic pixie dream girl, but MacLaine’s wondrous performance is far more complex than that. Few actresses have ever found the truth and pain of unrequited love, of despair, and of your life spiraling down the drain with as much lightness of touch or grace as MacLaine does here. Try to imagine the film without MacLaine and Lemmon, and you’ll see why we think they both should have won.
Paul Newman
Total Nominations: Ten in total, with one supporting nomination, for 2002’s “Road To Perdition,” one for Best Picture for “Rachel Rachel” in 1968, and eight in Best Actor, for “Cat On A Hot Tin Roof” (1958), “The Hustler” (1961), “Hud” (1963), “Cool Hand Luke” (1967), “Absence Of Malice” (1981), “The Verdict” (1982), “The Color Of Money” (1986) and “Nobody’s Fool” (1994). He also won an Honorary Award in 1986, and a Humanitarian award in 1994.
The Film He Won For: “The Color Of Money,” Martin Scorsese‘s 1986 sequel to one of Newman’s best known roles, in “The Hustler” (which he was also nominated for). Seeing Newman reprise Fast Eddie is an undeniable pleasure, but the film, an unusually anonymous and workmanlike one from the director, isn’t even the best performance the star gave as the character, let alone across his whole career. He’s very good, obviously, but if you were going to give one of the all-time great movie stars only one award for acting, why would it be for this movie? (Though in fairness, it wasn’t the most competitive year.)
The Film He Should Have Won For: Almost any of the other nominations would have done, including “The Hustler” (which has much more for Newman to play with), but we’d either go for the effortless charisma and iconic presence of “Cool Hand Luke,” or, if you’re going to award late-era Newman, 1981’s “The Verdict,” where Newman takes David Mamet‘s phenomenal screenplay about a faded alcoholic lawyer and plays it like a symphony.
Al Pacino
Total Nominations: Eight. Three in supporting—”The Godfather” (1972), “Dick Tracy” (1990) and “Glengarry Glen Ross” (1992)—and five in lead, including “Serpico” (1973), “The Godfather Part II” (1974), “Dog Day Afternoon” (1975), “…And Justice For All” (1979) and “Scent Of A Woman” (1992).
The Film He Won For: Hoo-hah! It was, of course, “Scent Of A Woman,” which has become something of a byword for the kind of odd, sorry-we-didn’t-do-this-earlier Academy decision that we’re talking about in this piece. Martin Brest‘s film isn’t bad, really, though it’s way too long and somewhat inconsequential in the grand scheme of things. And Pacino is pretty good in it, and clearly having fun, even if it clearly marks the start of his descent into the Shouty Al persona that we all know today. It’s far from Pacino’s last great performance (“Carlito’s Way,” “Donnie Brasco,” “The Insider” and “Insomnia” all were nomination-worthy), but to give him the award in the year of Denzel Washington‘s turn in “Malcolm X” (or, indeed, Robert Downey Jr. in “Chaplin” or Clint Eastwood in “Unforgiven,” also nominated alongside him) was insanity.
The Film He Should Have Won For: Bar “Dick Tracy” and “…And Justice For All,” any of his other nominations are deserving, but “Dog Day Afternoon” is our absolute fave. Sure, it might have elements of Shouty Al, but for the most part, Sidney Lumet‘s masterpiece lets Pacino play beautifully against type, a sensitive and brave performance that’s easily the most moving work he’s ever put on screen. Still, he was up against winner Jack Nicholson in “One Flew Over The Cuckoo’s Nest,” so it’s at least understandable why he missed out.