
Above, you see Amy Ryan from The Office. She plays the love interest of Michael Scott, and over the past couple years, she's been the best of all of his dates. You know, the sort of wacky, insane female match to his utterly insane character. However, in addition to playing Michael Scott's love interest on The Office, she also plays a harbor patrol cop in The Wire:

It reminds me of another actor, Omar Gooding. He first came up as a super colorful host of Wild and Crazy Kids:

And he progressed from that and roles on Hangin' With Mr. Cooper to being a drug-snorting nephew of Snoop Dog on the ultra-inappropriate ESPN show Playmakers:

Anyone else have some celebrity acting doppelgangers they like?
The first picture of Amy Ryan is from this site. The second picture is from here.