WWE Rooks: The Undertaker and Mankind
During the Monday Night War, two of the greatest rivals of all time were Undertaker and Mankind.
Before the advent of Mankind, Undertaker was nigh-invincible, only losing due to foul play and often taking on entire stables of wrestlers. Mankind humanized the Dead man, and made him a more believable character who could sometimes lose.
The pair are a good analogy for the Rook pieces because they're both imposing, capable of broad sweeping moves across the arena...or chess board...and were the pillars upon which the WWE rested during the Monday Night War.
WCW Rooks: Nature Boy Ric Flair and Arn Anderson
The Rook pieces in chess are meant to provide the stalwart defense and attack that is needed to protect the more vulnerable pieces, such as the King.
Ric Flair and Arn Anderson are perfect for this role. In many ways, they are the buttresses which helped prop up WCW during its very early, unprofitable years. They also represent the Four Horsemen, without whom there probably wouldn't have been a WCW, and therefore a Monday Night War.