46. Anthony Anderson
Approximate Weight: 250+ lbs.
Anthony Anderson may have got his start as a second banana, but his style is definitely worthy of leading man status. What he does well is wear things that complement his body type. Not too baggy, not too tight, just right. That's why suits look especially good on him, and his casual gear (down jackets, unbuttoned shirts) doesn't hang off his body. Hell, he can even wear tacky golf clothes and miraculously pull them off—he knows how to balance out crazy prints with solid colors.