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Here's a few ideas since I have no photoshop skills:
Gilligan's Island
Cassel as Gilligan
***** as the Skipper
The Jerk (Steve Martin)
Matt Cassel as "The Jerk"
Spaceballs
Clark as President Skroob
***** as Dark Helmet
Cassel as Colonel Sandurz
Romeo as Pizza the Hut
or
Clark as King Roland
***** as Prince Valium
Cassel as Princess Vespa
(these clowns could fit so many different roles in this movie)
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