Best Actor Oscar-Winners Since 2000, Ranked Worst to Best

Film

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

On April 25th, five men will square off at the Academy Awards for Best Actor — only one of them is walking away with the gold. The past two decades have seen a wide variety of performers claim this particular prize, everyone from French comic actors to veteran American stars, newcomers to established Hollywood names resurrecting their careers. Some of those performances already seem guaranteed to stand the test of time. Others … well, nobody’s perfect, especially Oscar voters, who often pick their winners for reasons that are unfathomable to the rest of us.

So in honor of the 93rd annual Academy Awards, we wanted to look back at the Best Actor champs of the 21st century to date, ranking them in order of greatness. A couple things we learned in the process, though: 1.) Playing a real person helps your chances of nabbing an Oscar (12 of the 20 winners fall into that category); and 2.) Your chances of winning go up immeasurably if you happen to be Sean Penn or Daniel Day-Lewis (they’ve both won two Oscars this century).

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