There are so many different types of pirates that it is difficult to choose just one.
Funniest - Johnny Depp as Capt. Jack Sparrow in POTC,
... Walter Mathau as Captain Red in Captain Red
Most classic fictional pirate - Geoffrey Rush as Capt. Barbossa in POTC
Most scary - Wallace Beery as Long John Silver in Treasure Island
Most musical - Tim Curry as Long John Silver in Muppets Treasure Island
Most unbelievable - Gina Davis as Morgan in Cutthroat Island (no woman is that strong)
Most athletic - Burt Lancaster as Capt. Vallo in the Crimson Pirate, Errol Flynn as Dr. Peter Blood
... in Captain Blood
So much for me 2 dubloons worth.
Jack II