Personal Supporting Actor Wins, 2000-16

Dafoe, Shadow of the Vampire
Kingsley, Sexy Beast
Cooper, Adaptation.
Bettany, Master and Commander
Law, I Heart Huckabee's (I figured I was the only one who even nominated him)
Collins Jr., Capote
Affleck, Hollywoodland
Affleck, The Assassination of Jesse James by the Coward Robert Ford (he's Lead, but I had to have a way to award him and DDL)
Ledger, The Dark Knight
Waltz, Inglorious Basterds

Garfield, The Social Network
Pitt, The Tree of Life
Hoffman, The Master
Hill, The Wolf of Wall Street
Norton, Birdman
Hardy, The Revenant
Rhodes, Moonlight

2000:Joaquin Phoenix, Gladiator
2001:Ben Kingsley, Sexy Beast
2002:Chris Cooper, Adaptation
2003:Alec Baldwin, The Cooler
2004:Clive Owen, Closer
2005:George Clooney, Syriana
2006:Mark Wahlburg, The Departed
2007:Javier Bardem, No country for old men
2008:Heath Ledger, The Dark Knight
2009:Matt Damon, Invictus
2010:Mark Ruffalo, Shutter Island
2011:Brad Pitt, The Tree of Life
2012:Leonardo DiCaprio, Django Unchained
2013:Jonah Hill, The Wolf of Wall Street
2014:Edward Norton, Birdman
2015:Will Poulter, The Revenant
2016:Mahershala Ali, Moonlight
2017:Will Poulter, Detroit

2000: Benicio Del Toro, Traffic
2001: Ben Kingsley, Sexy Beast
2002: Paul Newman, Road to Perdition
2003: Bill Nighy, Love Actually
2004: Thomas Haden Church, Sideways
2005: William Hurt, A History of Violence
2006: Eddie Murphy, Dreamgirls
2007: Javier Bardem, No Country for Old Men
2008: Heath Ledger, The Dark Knight
2009: Christoph Waltz, Inglourious Basterds

2010: Andrew Garfield, The Social Network
2011: Albert Brooks, Drive
2012: Phillip Seymour Hoffman, The Master
2013: Jared Leto, Dallas Buyers Club
2014: Edward Norton, Birdman
2015: Tom Hardy, The Revenant
2016: Mahershala Ali, Moonlight

2000: Joaquin Phoenix, Gladiator
2001: Steve Buscemi, Ghost World
2002: Alfred Molina, Frida
2003: Bobby Cannavale, The Station Agent
2004: Clive Owen, Closer
2005: Clifton Collins Jr., Capote
2006: Steve Carell, Little Miss Sunshine
2007: Paul Dano, There Will Be Blood
2008: Heath Ledger, The Dark Knight
2009: Christoph Waltz, Inglorious Basters
2010: Geoffrey Rush, The King's Speech
2011: Patton Oswalt, Young Adult
2012: Ezra Miller, The Perks of Being a Wallflower
2013: Jared Leto, Dallas Buyers Club
2014: Ethan Hawke, Boyhood
2015: Tom Hardy, The Revenant
2016: Trevante Rhodes, Moonlight

Albert Finney, Erin Brockovich
Steve Buscemi, Ghost World
Chris Cooper, Adaptation
Paul Bettany, Master and Comander
Thomas Haden Church, Sideways
William Hurt, A History of Violence
Michael Sheen, The Queen
Philip Seymour Hoffman, Charlie Wilson's War
Heath Ledger, The Dark Knight
Peter Capaldi, In the Loop
Mark Ruffalo, The Kids Are All Right

Philip Seymour Hoffman, Ides of March
Tommy Lee Jones, Lincoln
James Gandolfini, Enough Said
Helmut Berger, Saint Larent
Mark Rylance, Bridge of Spies
Humberto Carrao, Aquarius 

Blah, definitely my least favourite acting category. I'm totally on board with some of my picks but there are a few wasteland years with default choices ( last year might be the most precarious in a long, long time ) that makes it a weird list, however I love many performances I see mention above ( all the usual suspects, Bardem, del ToroX3, Affleck, etc ) but I consider all of them lead/co-leads.

2000: Benicio Del Toro, “Traffic”
2001: Steve Buscemi, “Ghost World”
2002: Ed Harris, “The Hours”
2003: Benicio Del Toro, “21 Grams”
2004: Clive Owen, “Closer”
2005: George Clooney, “Syriana”
2006: Alan Arkin, “Little Miss Sunshine”
2007: Javier Bardem, “No Country For Old Men”
2008: Heath Ledger, “The Dark Knight”
2009: Christoph Waltz, “Inglourious Basterds”

2010: Christian Bale, “The Fighter”
2011: Brad Pitt, “The Tree of Life”
2012: Phillip Seymor Hoffman, “The Master”
2013: Jake Gyllenhaal, “Prisoners”
2014: J. K. Simmons, “Whiplash”
2015: Benicio Del Toro, “Sicario”
2016: Ralph Fiennes, “A Bigger Splash”

As you can see, I fucking love Benicio Del Toro.

Albert Finney, Erin Brockovich
Justin Theroux, Mulholland Dr.
Chris Cooper, Adaptation
Stellan Skarsgård, Dogville
David Carradine, Kill Bill Vol 2
Clifton Collins Jr., Capote
Sergi López, Pans Labyrinth
Javier Bardem, No Country for Old Men
Eddie Marsan, Happy-Go-Lucky
Christoph Waltz, Inglourious Basterds
Christian Bale, The Fighter
Shahab Hosseini, A Seperation
Matthew McConaughey, Killer Joe
Matthew McConaughey, Mud
Taika Waititi, What We Do in the Shadows
Richard Jenkins, Bone Tomahawk
George MacKay, Captain Fantastic

2000: Brad Pitt, Snatch
2001: Ian McKellan, The Lord of the Rings: The Fellowship of the Ring
2002: Christopher Walken, Catch Me If You Can
2003: Sang-kyun Kim, Memories of Murder
2004: Clive Owen, Closer
2005: Jake Gyllenhaal, Brokeback Mountain
2006: Mark Wahlberg, The Departed
2007: Javier Bardem, No Country for Old Men
2008: Heath Ledger, The Dark Knight
2009: Christoph Waltz, Inglourious Basterds
2010: Christian Bale, The Fighter
2011: Nick Nolte, Warrior
2012: Phillip Seymour Hoffman, The Master
2013: Bill Nighy, About Time
2014: J.K. Simmons, Whiplash
2015: Tom Hardy, The Revenant
2016: Trevante Rhodes, Moonlight
2017 (so far): Will Poulter, Detroit

2000 - Ben Kingsley, Sexy Beast
2001 - Luke Wilson, The Royal Tenenbaums
2002 - Ray Liotta, Narc
2003 - Tim Robbins, Mystic River
2004 - Tom Cruise, Collateral
2005 - William Hurt, A History of Violence
2006 - Clive Owen, Inside Man
2007 - Ed Harris, Gone Baby Gone
2008 - Heath Ledger, The Dark Knight
2009 - Christoph Waltz, Inglourious Basterds

2010 - Christian Bale, The Fighter
2011 - Albert Brooks, Drive
2012 - Sam Rockwell, Seven Psychopaths
2013 - Jake Gyllenhaal, Prisoners
2014 - J.K. Simmons, Whiplash
2015 - Tom Hardy, The Revenant
2016 - Daniel Radcliffe, Swiss Army Man