Matt Damon Was Originally Going To Cameo In This Simpsons Episode

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"Lost Verizon" is a very 2008-style "Simpsons" episode. It takes place during that period where cell phones were becoming the norm, even among kids Bart's age, and bases its first act around Bart trying (and eventually succeeding) to get his hands on one. The fact that the cell phone's a flip phone immediately dates the episode, which is a shame because flip phones were very cool in the 2000s, and they allowed you to hang up angrily with dramatic, cinematic gusto. Nevertheless, the episode's main storyline ages perfectly: It's about Marge deciding to use Bart's phone to track his every move, a prescient commentary on the way cell phones have restricted kids' privacy despite their original promise of freedom.

But before "Lost Verizon" can deal with all of that, it must first introduce us to Denis Leary, the famous Massachusetts actor from "Rescue Me" and "Ice Age." Leary shows up at the Springfield golf course, crankily throwing away his phone in frustration and unwittingly fulfilling Bart's dream. It's a complicated guest star role; Leary's portrayed as cranky and vindictive at times, but he's also fairly cool about Bart using his phone. It's a fun role, although we can't help but wonder if it was originally intended for Matt Damon.

After all, when Variety wrote about the production for "Lost Verizon" in 2007, they sure seemed under the impression that Matt Damon would star in it. "Matt Damon is the catalyst for the hilarity in 'Lost Verizon,'" Variety wrote. "On the Fox lot, Nancy [Cartwright] drove us to her parking space in front of the small building where the reading was to take place. Hank Azaria walked in with us. Like Nancy, he plays several characters on the show. Hank also read Matt Damon's role since he isn't needed until later in the month for the actual recording session."

The episode ended up being delayed until season 20, and in that production gap it seems like Damon backed out. So, how did the show replace a household name like Matt Damon? It seems like they went with another Boston-based actor with a knack for playing angry, intense roles. There's no clear confirmation that Leary was Damon's replacement, but rewatching "Lost Verizon" it seems hard to imagine another role Damon could've fit. Besides a few digs at his Leary's TV career specifically, it feels like his character could've been Damon and nothing else about the episode would've changed.

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"Lost Verizon" is a typical season 20 episode in that it's not consistently hilarious like a classic-era "Simpsons" episode, but it's also nowhere near as bad as people might claim. I've always maintained that "The Simpsons" had a surprise boost in quality around seasons 18 through 21. Do I just think this because I was in middle school at the time? Maybe, but with the benefit of hindsight (and simply trying to view the later seasons of "The Simpsons" on their own terms), "Lost Verizon" is a perfectly fine episode. There are some great jokes here — such as Homer attempting to do laundry — and everything moves along at a brisk pace.

For some critics back in 2008, the episode's big flaw was how scattered its plot was. It "was not funny enough for such a serpentine storyline," wrote Robert Canning at IGN, arguing that the back-and-forth between Bart and Denis Leary should've been the episode's main plot, instead of veering off into Machu Picchu. Admittedly, it is easy to see a version of this episode revolving around a cat-and-mouse dynamic between Bart and Leary. In the few minutes the episode does dedicate to the two, Bart basically ruins Leary's life by signing him up for a terrible "Everybody Poops" movie adaptation and prank-calling bar owners around the globe. Having the second half of the episode being all about Leary trying to get revenge would've led to a more focused story.

On the other hand, I prefer the more grounded, emotional route the episode took. The final half of "Lost Verizon" does away with the show's constant celebrity guest cameos and keeps the episode all about Bart and Marge, who've always been one of the show's most underrated pairings. Marge starts the episode as a reasonable parent denying her kid a cell phone for sympathetic financial reasons, only to turn into an obsessive helicopter parent, before realizing that a more relaxed approach is probably healthier. Meanwhile, Bart starts the episode feeling restricted by Marge's parenting and then he achieves the full freedom he's always wanted, only to realize it's not what he needs. The episode's plot structure might seem wobbly and all-over-the-place at first glance, but it still gives us two focused, consistent character arcs bouncing off each other.

Is "Lost Verizon" the best episode of season 20? No, I'd give that title to "Gone Maggie Gone." But Matt Damon's absence aside, it's still a good episode of the show, and definitely worth the watch.