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The 500 Club in baseball is pretty elite. Only 25 players have swatted 500 home runs (and some of them sneaked in the door through dubious means). For prime time scripted entertainment series, the 500 Club (as in, episodes) is even more exclusive: There’s Gunsmoke and Lassie. Tonight The Simpsons will join that pantheon as the first comedy member with the airing of “At Long Last Leave,” in which Homer and Marge learn that Springfield’s residents are plotting to boot the family out of town for all the trouble they’ve caused over the years.

This milestone moment for the animated Fox series that has enjoyed a lot of them offers another chance for nostalgic reflection, which invariably leads to that question: What is your all-time favorite Simpsons episode? Hank Azaria — one of show’s key cast members who voices such beloved characters as Moe, Apu, Chief Wiggum, and Comic Book Guy – kindly agreed to go down that road with EW, though, as he notes, “it’s easy to narrow it down to 10 – then it gets really hard.” In his opinion, Season 5’s “Cape Feare,” in which Sideshow Bob attempts to kill Bart when he is sprung from prison, stands as the show’s biggest knee-slapper: “I laughed at that the hardest,” he says. “It just destroyed me from beginning to end. The rake thing is the hardest I ever laughed at a gag on The Simpsons. I love that humor where you just repeat something beyond all reason.”

His favorite episode, though, would be season 8’s “Homer’s Enemy,” in which the inept-and-loving-it Homer draws the ire of his new coworker at the nuclear power plant, Frank Grimes (voiced by Azaria). “I liked that it punched a hole not only in Homer but the whole tradition of: We just accept happy fat idiots in TV and film. They exist and they win. Why? What the hell?” Azaria explains. “[He] was sort of the voice of people who enjoy escaping in the show, or any comedy, like: ‘My life is hard. Why should I just accept that everything works out for some ridiculous character?’ Some of the best episodes are unbelievable social commentary — this one is not, but it was really funny. And the ending was just plain old dark. Just sad and weird, you know? It was an episode that played like an indie film.”

What does Azaria remember about recording that episode? “Often I will voice what will become the guest star role — just so we’ll have something to work with — and the guest star will come in and record it later,” he says. “Every once in awhile, what I record stands. That was one of those cases. William H. Macy was supposed to be Frank Grimes and wanted to do it, but I think it was a scheduling [conflict] and he ended up recording something for us later. But with William H. Macy in mind, although I can’t really imitate his voice, I did it. And it was probably some of the most serious acting I ever had to do, because the episode is so dark and the emotions are so real and raw. It was such a twisted episode. His rant where he’s just flipping out: ‘Oh, I’m Homer Simpson! I do whatever I want! Blahhh! Blahhh!’ — it was really fun to try to get it right. You know doing something that’s so well-written that you need to rise to what it is, even though it’s a cartoon … We did a bunch of takes. There were some where I freaked out more, there were some where I underplayed it. I was just doing that generic screaming, “Blahhh! Blahhh!,” to sort of rev up into the freak-out, but they ended up editing those in.”

Both of Azaria’s picks are sure to be cited by fans as they ponder their supreme Simpsons installment. As for me, I’ll go out on a half-inch limb by journeying to the early to mid-’90s as well. While several episodes from the Golden Age may contain sharper critiques or even pack more laughs per minute, I choo-choo-choose: Season 4’s salty-sweet “Duffless,” in which Homer gives up alcohol for a month at Marge’s request after an ill-fated journey to the Duff Brewery plant that ended with a DUI arrest. The show milked all kinds of laughs out of showing Homer’s struggle to untether himself from one of the great loves/crutches of his life. The Duff Brewery tour scene was a parade of punchlines, and the episode incorporated many of the dearest Simpsons hallmarks, including a conflict between Homer and his brain (mid-lie to Marge: “Uh-oh! Did I say that or just think it?”), a poignant musical parody “It was a Very Good Beer,” and a double dose of Phil Hartman as hammy has-been Troy McClure (“You may remember me from such films as Alice’s Adventures through the Windshield and The Decapitation of Larry Leadfoot“) and low-rent lawyer Lionel Hutz (“Surprise witnesses – each more surprising than the last!”). But wait, now that I mention Troy McClure, what about “A Fish Called Selma!”? And let’s not forget about “Last Exit to Springfield”? Or “I Love Lisa? Or “Marge vs. the Mono–” D’oh! Too much comedy awesome to process! Critics have already weighed in with their No. 1 pick here and here, so it’s your turn to declare your love for your favorite episode.

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