The Best Times Real Actors Played ‘Simpsons’ Characters In-Universe

Everyone knows that Dan Castellaneta has always played Homer Simpson, but even poor Ashley Grant and her “sweet can…” must admit that Dennis Franz did a decent cover.

For a seemingly unremarkable middle-class family in a small city, the Simpsons family sure seems to end up on TV a lot — usually in the news, occasionally in highly-dramatized made-for-TV movies that make sure to change just enough of the original story so that they don’t have to cut the Simpsons a check. The in-universe musicals, movies and TV shows of The Simpsons have created some of the most iconic moments in the show’s history — who doesn’t want to see a full-length version of Stop the Planet of the Apes I Want To Get Off! — but it’s extra special when we get to see the diegetic entertainment industry’s take on the characters we know so well, especially when they cast real-life actors to play them. There’s like 11 layers of meta that make those cameos so iconic.

Here are the top three times real-life actors played themselves playing Simpsons characters, starting with…

Neil Patrick Harris as Bart in ‘Blood on the Blackboard: The Bart Simpson Story’

Here’s a fun fact about the classic Simpsons Season Three episode “Bart the Murderer”: Despite the many plot similarities between the story of Bart’s induction into the Springfield mafia and the classic Scorsese film Goodfellas that came out the year prior, this episode was written before the movie, as was the made-for-TV movie starring Doogie Howser, M.D.

Though Fat Tony and the rest of his outfit tried to frame Bart for not just the murder of Seymour Skinner, but the entirety of their organized crime operation, Bart never pulled the trigger on his pesky principal. In fact, no one did — he was missing because he was buried underneath newspapers. That didn’t stop the makers of “Blood on the Blackboard: The Bart Simpson Story” from recruiting Richard Chamberlain, Joe Montagna, Jane Seymour and Neil Patrick Harris to dramatize the more salacious version of the story — and it gave the Simpsons producers and excuse to cast all those celebs as well.

Dennis Franz as Homer in ‘Portrait of An Ass-Grabber’

Though Homer’s name would eventually be cleared in the Easter egg-laden credits of “Rock Bottom,” anti-Homer sentiment hit its peak nationwide with the Fox: Night at the Movies retelling of the infamous incident regarding a feminist babysitter, a ride home and one particularly sweet can(dy). Dennis Franz’ Homer is only a slightly more reckless driver than the real deal, but his brutish, predatory performance was enough to shock a nation into uninformed outrage.

There is one issue with the portrayal worth noting, though it has nothing to do with Franz’ powerhouse performance — it’s a stretch for the writers of “Portrait of an Ass-Grabber” to assume that Homer knows who the president is, or what gender he or she may be.

Fyvush Finkel as Krusty in ‘The Krusty the Clown Story: Booze, Drugs, Guns, Lies, Blackmail and Laughter’

Krusty the Clown has led a roller-coaster, rock-star life, complete with all the ups and downs that come with being the most internally tortured TV clown in all of Springfield. It was only a matter of time before someone wised up and made a Baz Luhrmann Elvis-style celebrity biopic about his salacious escapades and problematic personal life — and Emmy-winner Philip “Fyvush” Finkel deserved another trophy for bringing Krusty’s rough edges to life.

Not only is this the meatiest role on the list with the most screen time, but the performance also contains one of the most comically out-of-left-field takedowns of Woody Allen in TV history — though Finkel would face stiff competition if we ever ranked the best Allen parodies on The Simpsons. McBain doesn’t seem like he’d settle for second place.

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