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