10 Best Simpsons Guest Stars (Who Played Themselves)

4. Darryl Strawberry

Simpsons Simon Cowell
20th Century Fox

Like Mick Jagger, you could really add ‘and the rest’ to Darryl Strawberry’s entry here. Unlike Mick Jagger’s episode (How I Spent My Strummer Vacation) though, Strawberry’s Homer At The Bat is a contender for an all time top ten.

While some examples here are from later episodes, they’re exceptions to the general rule that these days, the celebrity cameos are overused and undercooked. Back in the Golden Era though, when they got ahold of big stars they usually really delivered.

So when Mr Burns calls in a team of MLB athletes as ringers for his softball team, The Simpsons wrings every last bit of potential out of them. Right Fielder Darryl Strawberry is the only one who shows up to the game, with the rest of them suffering eight separate misfortunes.

From not understanding what Mr Burns means by sideburns, a bar fight with Barney over British Prime Ministers, gigantism, radiation poisoning or just falling into a void, each and every one of the players’ fates are comedy brilliance.

Strawberry gets the nod here because he has a bit more impact on the story, taking Homer’s position on the team. All of them are worthy of recognition though.

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