Will These Guys Ever Win Oscars? Part II - The 35-50 Crowd

With the fall film festival season behind us, the Oscar season is now pretty much in full swing, so we thought we’d take a look at some relate Oscar players who have never won Oscars (males now, females later) It’s been five years since Esquire magazine had Bill Murray on the cover along with the caption, “Will Somebody Please Give This Man An Oscar.” Since then, Bill has still come up empty handed, but he’s not alone. Here we’ve compiled a list of 22 male actors who’ve been nominated by the Academy for an acting award but have yet to take it home. But note, we’ve broken this up into three parts. Earlier today we ran, Part 1: The 50 And Above Crowd and now we’ve got, Part 2: The 40-50 Crowd. On Friday, we’ll deliver the 35 and below guys (hopefully).

Matt Damon (39)
Nominated For: “Good Will Hunting” – 1999 – Leading
Why He’s a Contender: Yes, Matt Damon did will an Oscar for “Good Will Hunting” (’98) but it wasn’t for his acting. Regardless, the nomination came fairly early in the actor’s career, so the win wasn’t likely. Now it’s been over ten years since playing the gifted janitor and he’s yet to garner another one, despite decent performances in films like “The Talented Mr. Ripley” (’99), “The Departed” (’06) and “Syriana” (’05), all of which earned his co-stars in those films supporting nods and a win in the latter’s case. Well this year, the wait might be over. Some are calling it “the year of Matt Damon” and even though his latest collaboration with Paul Greengrass (“Bourne Supremacy”/”Ultimatum“), titled, “The Green Zone,” was pushed back to 2010, Damon still has two other films in the can awaiting release. The first is a supporting turn in “Invictus” from Academy favorite Clint Eastwood, and the other, and more hopeful, is a leading role in Steven Soderbergh’s “The Informant!,” where he packed on the pounds like Academy Award winner, Russell Crowe, did for “The Insider” (’99). “The Informant!” may seem like a remake of that film, which earned Crowe his first Oscar nom, but while “The Insider” was a heavy drama, Damon’s film is an off-beat comedy. The year of Matt Damon? We shall see.

Paul Giamatti (42)
Nominated For: “Cinderella Man” – 2006 – Supporting
Why He’s a Contender: No, it’s not an error. Paul Giamatti does only have one Oscar nomination under his belt, and it’s not for “Sideways” (’04) either. After turning audience’s heads with “American Splendor” (’03) and then getting them to stand and cheer with the aforementioned ‘Sideways,’ the former character actor finally got his due playing the feisty corner man in Ron Howard’s boxing biopic, “Cinderella Man” (’05). Hopefully his time will come before he becomes a caricature of himself a la John Malkovich, who hasn’t won an Oscar yet either. Why It Might Never Happen: We mention this because like Malkovich, he’s already been reduced to playing himself on screen with this year’s “Cold Souls,” and there wasn’t anything spectacular about it in the least.

Mark Wahlberg (38)
Nominated For: “The Departed” – 2007 – Supporting
Why He’s a Contender: Even though Mark Wahlberg was scary as hell in the unnerving thriller “Fear” (’96), he didn’t get true recognition in the acting field until being cast as Dirk Diggler in Paul Thomas Anderson’s “Boogie Nights” (’97) the following year. As for his choices since then, they’ve been pretty shoddy, save for “Three Kings” (’99). That was until his unexpected comedic performance in his second David O. Russell film, “I Heart Huckabees” in 2004. In 2006, Wahlberg co-starred as a smart-alecky police sergeant with a think Boston accent in “The Departed,” and even though it starred four other Oscar nominated actors, he was the only one who landed a nom for it. You can see Wahlberg later this year as a grieving father in “The Lovely Bones,” since he replaced Ryan Gosling in the role. Director Peter Jackson has been quoted saying he liked Wahlberg’s slightly nutty quality he showed in his ‘Huckabees’ performance, and they used that as a spring board for ‘Bones,’ though obviously toned it down. Also in current development is his third O. Russell film, the previous Darren Aronofsky project, “The Fighter.” Wahlberg has been physically training seemingly forever is preparation for his portrayal of real-life Irish boxer, Mickey Ward, who the film is about, and we all know how the Academy likes to see some physical alteration, even though that hasn’t helped the constant weight fluctuating Christian Bale, who co-stars in the film, get an Oscar nomination of his own.

Brad Pitt (45)
Nominated For: “Twelve Monkeys” – 1996 – Supporting
“The Curious Case of Benjamin Button” – 2009 – Leading
Why He’s a Contender: Being the most popular actor in the world doesn’t mean you’re the most acclaimed, and such is the case with Brad Pitt. Even though we think Pitt should’ve gotten some Academy recognition for his supporting role in “A River Runs Through It” (’92), he didn’t earn his first nomination until playing the colorfully eccentric, Jeffrey Goines, in “Twelve Monkeys” (’95). It has since taken Pitt thirteen years to get another one, after “Babel” (’06) and “The Assassination of Jesse James” (’07) didn’t quite connect with audiences. Not that his performance in ‘Benjamin Button’ did with us, but we see it as one of those infamous Academy make-up nominations. Already this year, Pitt has had a cheeky supporting role in “Inglourious Basterds,” and although he’s good with what he does in the film, it’s more of a fun diversion a la “Snatch” (’00) or “Burn After Reading” (’08) than a serious awards contender. He’s also set to appear in Terrence Malick’s “Tree of Life” along with Sean Penn, but so little is know about the film at this point, including when it is going to be released, it makes it difficult to speculate.

Edward Norton (40)
Nominated For: “Primal Fear” – 1997 – Supporting
“American History X” – 1999 – Leading
Why He’s a Contender: We can’t think of another actor that started his career as strong, and with as much potential, as Edward Norton. Right out of the gate, Norton landed a supporting Oscar nomination with his first film, “Primal Fear” (’96). Of course he didn’t win, or else he wouldn’t be on this list, but after a couple more promising performances in “The People vs. Larry Flynt” (’96) and “Rounders” (’97), Norton scored a second nom a mere two years later. This time it was for his leading role as the violent skin head in “American History X” (’98). Here is where we think Norton should’ve taken home the statue and not just because he was scarily good, but because after you judge his competition, including the winner that year, Roberto Benigni, we don’t even think it was a contest. Nevertheless, we surely didn’t think that would be his last Oscar nom to date given his output in that short span. So far, we’ve been proven wrong though, as Norton is never bad in a film but he just hasn’t been as good. Lately, he’s been busy trying to revive a superhero franchise and documenting president Obama, so the lack of an Oscar must not be bugging him as much as it is us. Norton will star as twins in the upcoming “Leaves of Grass,” so if his performances are anywhere near as good as Nicolas Cage’s were in “Adaptation” (’02), he could have a shot.

Robert Downey Jr. (44)
Nominated For: “Chaplin” – 1993 – Leading
“Tropic Thunder” – 2009 – Supporting
Why He’s a Contender: Even more than Brad Pitt’s thirteen year separation between Oscar nominations is Robert Downey Jr.’s sixteen year absence from the ceremonies. Now we’re not sure where he’s been, but we do know he’s back and hotter than ever. With the success of “Iron Man” (’08) and strong showings in “Kiss Kiss Bang Bang” (’05), “A Scanner Darkly” (’06) and “Zodiac” (’07), Robert Downey Jr. is easily holding his own these days. Sometimes criticized for “playing himself,” the same could be said for Bill Murray, and in our opinion is a weak argument. Now we didn’t think his addition to “Tropic Thunder” (’08) was necessarily Oscar worthy, but we don’t think he probably did either. We’re not sure about his prospects this year however. “The Soloist,” like “The Road,” was originally scheduled for an awards season release last year, but then was pushed back. It was then released too early this year and will since be forgotten. “Sherlock Holmes,” on the other hand, is set for release on Christmas Day, but seems far too light and from what we’ve seen in the trailer, might not impress.

Jude Law (36)
Nominated For: “The Talented Mr. Ripley” – 2000 – Supporting
“Cold Mountain” – 2004 – Leading
Why He’s a Contender: Jude Law first caught our attention when he co-starred in “Gattaca” in 1997, but it wasn’t until 1999 when he co-starred in “The Talented Mr. Ripley” that he proved he brought more than good looks to a film. We thought his nomination for “Cold Mountain” (’03) wasn’t quite deserved, as he seemed a bit awkward in the film, and would’ve rather seen him nomed for supporting again the next year for “I Heart Huckabees” (’04), as we think that is some of his best work and sadly underappreciated. We will say we’ve noticed a dislike for Law amongst some of the film critic community, so maybe he does have to prove he’s not just a pretty face. Coming up, Law fills in for Heath Ledger in the late actor’s final film appearance, “The Imaginarium of Doctor Parnassus.” There’s also “Sherlock Holmes” but Law has about as much a chance at getting an Oscar for it as Robert Downey Jr. does, which may be slim to none.

Ralph Fiennes (46)
Nominated For: “Schindler’s List” – 1994 – Supporting
“The English Patient” – 1997 – Leading
Why He’s a Contender: We know what you’re thinking; “I thought that guy has won an Oscar before.” That tends to be the consensus among the general population, so don’t feel bad. But no, despite starring in two of the most Oscar nominated films of all-time, Ralph Fiennes has none of his own. In fact, he jokes about this in the teaser trailer for the upcoming “Cemetery Junction” (’10) with co-star/director, Ricky Gervais, driving the point home. Fiennes is pretty consistent though. Last year he had two good supporting roles with “In Bruges” and “The Reader,” so we’re not too worried about him. We’ll just be glad when the “Harry Potters” are finished so he can concentrate on more important films.

Will Smith (41)
Nominated For: “Ali” – 2002 – Leading
“The Pursuit of Happyness” – 2007 – Leading
Why He’s a Contender: Who would’ve thought the goofy, sarcastic kid from “The Fresh Prince of Bel Air” TV show would be receiving Oscar nominations not long after? Not us, that’s for sure. Naturally, Will Smith isn’t the best thespian in the biz and sure he still makes the majority of his money making big budget crapola, but now he’s learned to throw in a dramatic role here and there, if for nothing else, to prove to everyone he’s a real actor. The first time he tried this was in 2000 under the direction of Robert Redford in “The Legend of Bagger Vance.” That must’ve been batting practice because his next film was “Ali” (’01), where he hit it out of the park and scored his first Oscar nom. A few crappy sequels later, he was back with “The Pursuit of Happyness” (’06), and just last year, attempted to recreate that winning formula with “Seven Pounds” (’08) but to no avail. Now he’s adding remakes of films that don’t need to be remade to his resume with “Old Boy,” and even more crappy sequels, this time for films that were crappy to begin with, with “Hancock 2.

Tom Cruise (47)
Nominated For: “Born on the Fourth of July” – 1990 – Leading “Jerry Maguire” – 1997 – Leading
“Magnolia” – 2000 – Supporting
Why He’s a Contender: No matter what you think about Tom Cruise these days, even we think he’s a bit crazy, you can’t deny the consistency of the performances he’s put in from the 80’s throughout the 90’s. He popped onto everyone’s radar with the smash hit “Top Gun” in 1986, but didn’t show his acting chops until playing Dustin Hoffman’s conflicted brother in “Rain Man” in 1988. We all know Hoffman won an Oscar for his performance in that film, but think Cruise more than deserved a nomination himself. He got his due the following year however, when he landed a leading actor nomination portraying a paralyzed war vet in “Born on the Fourth of July” (’89). Daniel Day Lewis would go on to win the Oscar that year for his own interpretation of a paralyzed man in “My Left Foot” (’89), but we still firmly believe Cruise deserved the win. Daniel Day Lewis is a terrific actor, no doubt about it, and his performance was definitely above par, but after witnessing the emotional tour de force Cruise put forth, we can’t understand how more people didn’t side with us. Cruise didn’t let the loss slow him down any, and after terrific leading roles as hot shot lawyers in “A Few Good Men” (’92) and “The Firm” (’93), and a showing supporting one opposite Brad Pitt in “Interview with the Vampire” (’94), Cruise was back at the Oscars for “Jerry Maguire” (’96). He obviously lost, and then lost again for his dynamic contribution to “Magnolia” (’99). Since then, “Collateral” (’04) has been his only performance worth writing home about, as we think his extended cameo in “Tropic Thunder” (’08) is overrated. Today, Cruise seems slow to commit to any projects, but we think if he can overcome his public perception, he could win back a couple of fans and maybe an Oscar to boot.

Johnny Depp (46)
Nominated For: “Pirates of the Caribbean: The Curse of the Black Pearl” – 2004 – Leading
“Finding Neverland” – 2005 – Leading
“Sweeny Todd: The Demon Barber of Fleet Street” – 2008 – Leading
Why He’s a Contender: It’s hard to believe Johnny Depp didn’t receive his first Oscar nomination until 2004, and for a big budget blockbuster based on a Disney World kids ride at that! Not that we didn’t enjoy Depp’s invention of the flamboyant Jack Sparrow, but how about the dozen diverse roles before that? We firmly believe Depp should’ve been nominated, and possibly should’ve won, ten years prior for his hysterically naïve “Ed Wood” (’94), easily Depp’s finest hour. Maybe he was snubbed because comedic performances rarely get nominated for leading actor, but Depp overcame that with his nom for “Pirates of the Caribbean” (’03) and Depp isn’t even a comedian. Oh well, at least now he’s got the ball rolling. His portrayal of John Dillinger in this year’s “Public Enemies” was serviceable, but we wouldn’t hold our breath. Later this year, Depp fills in for Heath Ledger in the late actor’s final film appearance, “The Imaginarium of Doctor Parnassus.” Next year, we’ll get to view his version of the Mad Hatter in “Alice in Wonderland,” but are afraid it might just be a rehash of his quirky Willy Wonka. Also anticipated is “The Rum Diary,” another stab at Hunter S. Thompson, who Depp wonderfully channeled in “Fear and Loathing in Las Vegas” (’98). — Jonathan Helm