PopWatch Matchmaker: Robin Williams’ Simon Roberts and Marcia Gay Harden’s Diane Buckley

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Image Credit: Monty Brinton/CBS;Bob D'Amico/ABC

Some of our favorite TV characters are often unlucky in love. They just can’t seem to find The One — but what if The One is on another show altogether?

Okay, I’ve got one for you. What do you get when you mix vicious one-liners with endless rants? A hard-to-crack doctor and a cracked-up ad man? An explosive combination of comedy that can’t decide whether to be pithy or long-winded. That’s what you get in my PopWatch Matchmaker proposal: Diane from Trophy Wife and Simon from The Crazy Ones.

It’s a tough order to find Robin Williams a suitable onscreen mate that can match him riff-for-riff (to date, my favorite Williams screen spouse is Sally Field in Mrs. Doubtfire, but she basically didn’t do anything except yell “Oh my God!” the whole time). But Williams’ eccentric ad exec Simon Roberts could be absolutely for one of the fall TV season’s breakout characters: Marcia Gay Harden’s steely ice queen Diane, an ex-wife from hell whose totalitarian approach to parenting is twice as hilarious as it is terrifying.

It’s in this rare attraction of opposites that I think sparks might fly between these two polar opposites. He’s wacky, untamed, and frequently dives into impressions that Diane would simply label “unnecessary.” She’s hard to impress, cold, terse, and prone to using her cunning evils to trick her children into fearing — and thereby loving — her. I imagine that Simon would be up for the challenge of trying to crack Diane’s hard, laughless shell, while Diane would likely see the opportunity for victory if she can reign in man-child Simon and put the wild beast on a leash. Weirdly, it works, right?

Not to mention that Diane’s rapid-fire wit and razor-sharp tongue could easily whip up any number of speedy put-downs to respond to Simon’s ranting jokes — and vice versa, of course. Diane’s cold and calculated; Simon’s fast and funny — I smell a sitcom!

Bonus Matchmaker: The merging of these two worlds would also mean that Diane’s children Warren (Ryan Lee) and Hillary (Bailee Madison) would then be brethren to Simon’s frantic daughter Sydney (Sarah Michelle Gellar), which is itself a hilarious match-up of insecure, screwed-up children whose parents have left their mark of insanity.


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