The Killing Lady & Dylan Baker, who plays preachers a lot

   

Mireille Enos of AMC's The Killing looks a lot like Dylan Baker of Amy Sedaris's Strangers With Candy (et al). You could use this casting for a movie where transgendered lookalikes trade families but the families are so bland, they decide to just be together instead and go on a bank robbing spree because look at that face! Who would suspect that face?

Benicio Del Toro & Brad Pitt when they both have beards

    

"These beards...they weigh our faces down so that we have to squint and feel stress in our forehead areas."

Timothy Busfield & A.D. Miles

    

Poindexter from Revenge of the Nerds is quite possibly the best redhead in the world, period. And A.D. Miles looks enough like him to make me go ahead and say it: They were WRONG for shelving the Revenge of the Nerds reboot and they will LIVE to regret it. Also, A.D. Miles is a very good redhead.

A.D. Miles and Timothy Busfield forever!

Tracy Reiner (Betty Spaghetti) & Janice from The Sopranos

   

Lo and behold, Betty Spaghetti was not played by Tony Soprano's sister! Doesn't it seem like she was, though? Betty Spaghetti was actually played by Tracy Reiner, who is Penny Marshall's daughter and Rob Reiner's step-daughter. Janice Baccalieri nee Soprano was played by Aida Turturro, who is cousins with John (at least according to Wikipedia). These are not the same actress. I'm positive.