Bill Hader as Richie

Of all the casting suggestions made here, this is admittedly my favorite. For the role of adult Richie, Finn Wolfhard suggested that Bill Hader be given a shot, and it's really a perfect fit. Not only is there a similarity in the looks department, as seen in the side-by-side above, but Hader's natural personality just makes him a perfect fit for the character.

As a kid, Richie stands out as a jokey loudmouth who doesn't know when to shut the hell up, but it's a gift that actually winds up suiting him well professionally. His gift for gab gets him a cushy job as a Los Angeles radio personality, where he has the freedom to be his natural comedic self. If you don't see how Bill Hader is an obvious choice here, I don't know what to tell you.

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