Last April, I came up with my personal list of the 2o Most Deserving Oscar Best Actress Wins wherein Olivia de Havilland’s The Heiress prevailed on top (which is currently being performed on Broadway by the great Jessica Chastain). Now, this is the second part of the four acting categories that I will be doing. In this part, the ladies have to sit down as the men takes center stage. The Best Supporting Oscar has been a venue of rewarding a lot of character actors and veterans way back from Walter Brennan’s first victory for Come and Get It in 1936 up to current champ’s Christopher Plummer’s win for Beginners just earlier this year. Of the 76 victories in this category, here are 20 performances that stood out from the rest:

20. MICHAEL CAINE, “Hannah and Her Sisters” (1986)

Role: Elliott, husband of actress Hannah who has an affair with one of his wife’s sister
Competition: Tom Berenger (Platoon), Willem Dafoe (Platoon), Denholm Elliott (A Room With a View), Dennis Hopper (Hoosiers)

Two time winner here in this category, Sir Michael Caine has yet to win a Lead Actor Oscar, but his two victories in the Supporting ones are some of his best performances. In particular, his performance in Woody Allen’s Hannah and Her Sisters takes the cake and deserves a slot in the top 20.

19. GEORGE CHAKIRIS, “West Side Story” (1961)

Role: Bernardo Nunez, head of the gang of Puerto Rican immigrants in Manhattan
Competition: Montgomery Cliff (Judgment at Nuremberg), Peter Falk (Pocketful of Mysteries), Jackie Gleason (The Hustler), George C. Scott (The Hustler)

Whether it’s the musical numbers or the slick choreography that you admire the most in this Best Picture winner, one can’t deny that lots of it has something to do with George Chakiris’ lively and energizing performance as Bernardo Nunez. That, and his chemistry with Rita Moreno’s Anita.

18. JOEL GREY, “Cabaret” (1972)

Role: Master of Ceremonies, the storyteller in the film
Competition: Eddie Albert (The Heartbreak Kid), James Caan (The Godfather), Robert Duvall (The Godfather), Al Pacino (The Godfather)

From one musical to the other, George Chakiris’ performance as the storyteller slash master of ceremonies in the film can be easily played by a nameless actor, but the way that he engaged the watchers is credited to his immense talent. This surely worked in his favor, as he managed to win over three Godfather actors in this category.

17. JACK NICHOLSON, “Terms of Endearment” (1983)

Role: Garrett Breedlove, womanizing neighbor of Aurora who is afraid of commitment
Competition: Charles Durning (To Be or Not to Be), John Lithgow (Terms of Endearment), Sam Shepard (The Right Stuff), Rip Torn (Cross Creek)

The most rewarded male actor by the Academy, Nicholson’s only win in the Supporting category (out of four nominations), is also one of his bests. As someone who is afraid of commitment, thus resulting to having cold feet in his relationship to Shirley Maclaine’s Aurora, Nicholson not only relied to his physical charisma but providing the emotional gravitas needed a well.

16. DENZEL WASHINGTON, “Glory” (1989)

Role: Pvt Silas Trip, escaped slave who joined the Massachusetts Infantry Regiment
Competition: Danny Aiello (Do the Right Thing), Danny Aykroyd (Driving Miss Daisy), Marlon Brando (A Dry White Season), Martin Landau (Crimes and Misdemeanors)

Two years after his pilot nomination for Cry Freedom, Washington comes back in full glory (no pun intended) as the standout among the crop of supporting actors in this film. In Glory, Denzel was all out in showing his potential to be one of the best actors in his generation, and the same can still be said about him today.

15. BENICIO DEL TORO, “Traffic” (2000)

Role: Javier Rodriguez, police officer responsible for the revealing of drug transport in Mexico
Competition: Jeff Bridges (The Contender), Willem Dafoe (Shadows of the Vampire), Albert Finney (Erin Brockovich), Joaquin Phoenix (Gladiator)

It’s really difficult to stand out in an ensemble such as the one in Traffic. But while we can credit Stephen Gaghan’s multi-layered script, or the sharp direction of Steven Soderbergh, there’s a reason why it was only Puerto Rican Benicio del Toro who was nominated among the cast. His Javier Rodriguez was a one two combo of his balanced portrayal of an honest yet haunting officer.

14. EDMUND GWENN, “Miracle on 34th Street” (1947)

Role: Kris Kringle, Santa Claus at the Macy’s Thanksgiving Parade
Competition: Charles Bickford (The Farmer’s Daughter), Thomas Gomez (Ride the Pink Horse), Robert Ryan (Crossfire), Richard Widmark (Kiss of Death)

Probably one of the most known characters in this list, Gwenn’s performance as the Santa Clause in 1947’s Miracle on 34th Street is no way miraculous. It was already given by the get go that his poignant turn deserves merit, and Oscar fortunately agrees with me on this one.

13. JOE PESCI, “Goodfellas” (1990)

Role: Tommy DeVito, robber part of a local mob
Competition: Bruce Davison (Longtime Companion), Andy Garcia (The Godfather Part III), Graham Greene (Dances with Wolves), Al Pacino (Dick Tracy)

Mob movies and characters from such have been a staple in this category that many tried to replicate but not give justice to the said genre. One of the exceptions though is Joe Pesci’s Tommy DeVito in this Best Picture nominee. Now if only we can have Damian say “Danny Tommy DeVito I love your work”, then that would be the cherry on top of this cake.

12. KARL MALDEN, “A Streetcar Named Desire” (1951)

Role: Harold Mitchell, a suitor of Vivian Leigh’s Blanche Dubois
Competition: Leo Genn (Quo Vadis), Kevin McCarthy (Death of a Salesman), Peter Ustinov (Quo Vadis), Gig Young (Come Fill the Cup)

Another movie that stood the test of time, A Streetcar Named Desire has been mostly remembered for the performances of Marlon Brando or Vivien Leigh, or the countless adaptations that has been produced in Broadway or in the small screen. But here’s one FYC: Do not forget to check out Karl Malden’s Oscar winning performance in it, and you’ll understand why.

11. CHRIS COOPER, “Adaptation” (2002)

Role: John Laroche, orchid expert who helped Susan Orleans in her book writing
Competition: Ed Harris (The Hours), Paul Newman (Road to Perdition), John C> Reilly (Chicago), Christopher Walken (Catch Me If You Can)

To share most of your time onscreen with Meryl Streep is a very daunting task. Awards-wise, you’d always fade away and nominations seem to be unlucky just like Sam Neill in A Cry in the Dark, Stanley Tucci in Julie and Julia, the ladies of The Devil Wears Prada, and even Clint Eastwood in The Bridges of Madison County. The most you can have is a nomination just like the triumvirate in Doubt. The only exception though is 2002 winner Chris Cooper who not only shared a perfect chemistry with Streep herself, but he even went home with an Oscar on his hand.

10. KEVIN KLINE, “A Fish Called Wanda” (1988)

Role: Otto West, a self proclaimed intellectual recruited to be a part of a jewel heist
Competition: Alec Guinness (Little Dorrit), Martin Landau (Tucker: The Man and His Dream), River Phoenix (Running on Empty), Dean Stockwell (Married to the Mob)

Comedies rarely get any recognition outside of the Golden Globes, so it is always refreshing to see actors win Oscars for comedic performances such as this victory of Kevin Kline in 1988 for his role as a part of a jewel heist in A Fish Called Wanda. This gives us reassurance that every now and then, Oscar knows his humor.

09. KEVIN SPACEY, “The Usual Suspects” (1995)

Role: Roger Kint, survivor of a massacre up for interrogation
Competition: James Cromwell (Babe), Ed Harris (Apollo 13), Brad Pitt (12 Monkeys), Tim Roth (Rob Roy)

Another two time Oscar winner, Kevin Spacey’s first Oscar was in the supporting category for this flexible and layered performance as one of the two survivors in 1995’s The Usual Suspects. It’s really hard to argue with the Academy when they give very deserved wins such as this one.

08. GEORGE SANDERS, “All About Eve” (1950)

Role: Addison DeWitt, theater critic who is observant of Eve’s career
Competition: Jeff Chandler (Broken Arrow), Edmund Gwenn (Mister 880), Sam Jaffe (The Asphalt Jungle), Erich von Stroheim (Sunset Boulevard)

While all the buzz was between the leading ladies of this 1950 Best Picture title holder, George Sanders made sure that he will not be forgotten and that he will make a mark for his performance in his film. Alas, not only is he rewarded with an Oscar, his victory is also one of the best this category has ever produced.

07. TIMOTHY HUTTON, “Ordinary People” (1980)

Role: Conrad Jarrett, son of a dysfunctional family who recovered from a failed suicide attempt
Competition:  Judd Hirsch (Ordinary People), Michael O’Keefe (The Great Santini), Joe Pesci (Raging Bull), Jason Robards (Melvin and Howard)

Like what I mentioned, the Supporting Actor category has been a venue to reward character actors or older veteran ones. That is why, category confusion aside, it is very refreshing to see victories such as this one by Timothy Hutton as the troubled son of a dysfunctional family in Ordinary People. His performance, definitely, is far from ordinary in it.

06. WALTER HUSTON, “Treasure of Sierra Madre” (1948)

Role: Howard, an old man part of the triumvirate planning to search for gold
Competition: Charles Bickford (Johnny Belinda), Jose Ferrer (Joan of Arc), Oskar Homolka (I Remember Mama), Cecil Kellaway (The Luck of the Irish)

Probably one of the most remembered winning performances in this category, it is really not difficult to fathom why Walter Huston won in 1948. It’s the typical supporting turn that tends to scream “scene stealer!” With that said, it will be difficult to pre-judge a scene stealer like Howard, when he nails it in and out in this performance.

05. CHRISTOPH WALTZ, “Inglourious Basterds” (2009)

Role: Hans Landa, a ruthless yet charming Austrian officer searching for Jews all over France
Competition: Matt Damon (Invictus), Woody Harrelson (The Messenger), Christopher Plummer (The Last Station), Stanley Tucci (The Lovely Bones)

The last of the triumvirate of the bad guys rewarded in this category during the last decade, who knew that at 52, TV actor Christoph Waltz will waltz his way (this time, pun intended) to a unanimous award acclaim for his performance as Colonel Hands Landa in this Tarantino flick. What I particularly loved about Landa is that while you know he’s the bad guy, it’s easy to see his soft spots as well. This, I credit, to Christoph Waltz’s bravura performance.

04. HEATH LEDGER, “The Dark Knight” (2008)

Role: The Joker, antagonist to Bruce Bayne’s Batman
Competition: Josh Brolin (Milk), Robert Downey Jr (Tropic Thunder), Philip Seymour Hoffman (Doubt), Michael Shannon (Revolutionary Road)

While one can still see the good in Hans Landa, it’s easy to spot the not so good in terms of Heath Ledger’s Joker. Despite it being a posthumous win, it really did not overshadow the fact that this performance has been the best among all of Nolan’s Batman trilogy, and probably will be the most iconic too. When the only bad thing you can say about Ledger’s Joker are the character’s intentions, you know that this one is for keeps.

03. JAVIER BARDEM, “No Country for Old Men” (2007)

Role: Anton Chigurh, hitman who plays a cat and mouse chase with Josh Brolin’s Llewelyn Moss
Competition: Casey Affleck (Assassination of Jesse James by the Coward Robert Ford), Philip Seymour Hoffman (Charlie Wilson’s War),  Hal Holbrook (Into the Wild), Tom Wilkinson (Michael Clayton)

Before Joker and Col. Landa took over the “bad guy” territory, everyone felt the chills as Javier Bardem sneaked his way in and out of Texas searching for Llewelyn Moss. You can laugh all you want about Javier Bardem’s bad hairdo in the film, but there’s nothing bad you can say about this universally acclaimed performance of his. The near end shot of him with his face bloodied yet still alive is one of the creepiest you’ll see in a film that’s not about ghosts.

02. ROBERT DE NIRO, “The Godfather Part II” (1974)

Role: Don Vito Corleone in flashbacks
Competition: Fred Astaire (The Towering Inferno), Jeff Bridges (Thunderbolt and Lightfoot), Michael V. Gazzo (The Godfather Part II), Lee Strasberg (The Godfather Part II)

When we’re talking about The Godfather, it’s really impossible to pass on the topic of the performances of the actors in the trilogy. Given that condition, it is more difficult when you’re playing Don Vito Corleone whose character already won itself an Oscar two years ago in the Lead Actor category by Marlon Brando nonetheless. But thanks to Robert de Niro’s effortless yet memorable performance, not only does this role scoop another Oscar, but de Niro’s performance and win is also the second best win in this category.

01. CHRISTOPHER WALKEN, “The Deer Hunter” (1978)

Role: Nikonar Chevotarevich, steel worker who serviced during the Vietnam War
Competition: Bruce Dern (Coming Home), Richard Farnsworth (Comes a Horsemen), John Hurt (Midnight Express), Jack Warden (Heaven Can Wait)

And the champion among all champions is none other than… Christopher Walken. Michael Cimino’s Best Picture winner in 1978 not only provided controversy during its time, his terrific direction also gave us a lot of performances to cherish. One of those is Christopher Walken’s heartbreaking, honest, and raw performance as Nikonar Chevotarevich. Despite the backlash the movie has received during the awards season that year, the acclaim for the performance (particularly of Walken’s) has even naysayers rooting for it.

There you go! What are your favorite inclusions on the list? How about the ones you think should have been excluded? Also, are there missing performances you want to lobby for? Pipe them in below!  🙂