This Sandlot Star Grew Up To Be Unrecognizably Gorgeous

Chauncey Leopardi, better known as Michael "Squints" Palledorous, will go down in cinema history for the stunt he pulled at the community pool in the summer of 1962. After diving into the deep end in 1993's The Sandlot, the fifth-grader is rescued by the sizzling hot Wendy Peffercorn — several years his senior — and given mouth-to-mouth resuscitation before revealing the whole thing to be a ruse in a wink towards his friends.

The move may have gotten him and his crew banned from the pool, but it also cemented their status as movie icons as The Sandlot grew to be a cult classic. The flick follows the group over a scenic '60s summer after they lose a baseball signed by Babe Ruth in a neighbor's backyard, and attempt to rescue it from a dog aptly named "The Beast." While Leopardi may never live down his role as the bespectacled smart aleck, he doesn't need to. 

Not only has the grown-up star ditched the glasses — he says his vision was always impeccable — and embraced the sports film's legacy, but he's grown up into a swoon-worthy hunk with a heart. Tackling love, fatherhood, Hollywood, and entrepreneurship over the years, it's no surprise that Squints had a major "glow up," while the movie that started it all continues to get bigger.

Like his iconic line, Chauncey Leopardi will be associated with his Sandlot character "for-ev-er." However, fans might be surprised to learn that he originally auditioned for Marty York's character, Alan "Yeah Yeah" McClennan. At 11-years-old, Leopardi eventually won the role after nearly five rounds of auditions with some past baseball experience. "I was athletic enough that I could play anything," he told The Score. "It wasn't really a big deal." His character, nicknamed Squints for his specs, is known for his wisecracks and romantic pursuits. An integral member of the baseball team, he provides plenty of comic relief throughout the film with quips like "Hurry up, my clothes are going out of style" — a favorite of Leopardi's (via Green Bay Press Gazette) — and his lip-lock with the lifeguard. 

While the film made a mediocre $32 million during its theatrical run, it clearly struck a chord with audiences. Patrick Renna, who portrayed Sandlot favorite Ham, told Den of Geek that it wasn't until the 20th anniversary that they recognized its "staying power." Nowadays, the cast has a group chat and "see each other a lot." Leopardi continues doing press for its milestones, telling USA Today it's "surreal" to be celebrating decades later, adding "when you do a film you never have any idea that it's going to be any good, let alone stand the test of time."

Things ended pretty well on the big screen for Squints and his lifeguard crush Wendy Peffercorn in The Sandlot: in the end, it's revealed they get married and have a whopping nine kids. Chauncey Leopardi and co-star Marley Shelton, however, didn't quite share the same chemistry. Despite their seven-year age gap, Sandlot director David Evans told the San Antonio Current that he remembers Leopardi being quite the "little player" on-set. For his part, Leopardi still recounts the pool scene as his favorite, telling fans at a 2019 event (via Alamo Drafthouse), "You always remember your first kiss."

Although they shared that magic moment, Leopardi told the Green Bay Press Gazette he hadn't seen Shelton in 25 years since the film's premiere, but they later reconnected at an anniversary event in 2018. As for Shelton, she told US Weekly that she's "shocked" by the film's legacy. "Nobody thought it was going to have the legs that it did and become this cult classic," Shelton added, though she feels "flattered" to still be recognized for the steamy role. 

Shelton is married to Skyscraper and Rampage producer Beau Flynn, and the two are always amused by the countless Halloween costumes inspired by her swimsuit. "There are some great costumes out there that probably rival the original," she said. According to People, Shelton and Flynn married in 2001 and have two daughters together.

Hollywood wasn't always front-of-mind for Chauncey Leopardi. In fact, he was discovered in Dallas at six-years-old while accompanying his cousin to an agency audition. "I was just along for the ride," he said in a 2008 interview with the RobotBitesMan blog, adding, "But I had this really long hair and tons of energy." He eventually moved to Los Angeles at age seven, booking roles in 1991's Father of the Bride and the Boy Meets World pilot before scoring The Sandlot, which hit theaters in 1993. Throughout the '90s, he appeared in 7th Heaven, Walker, Texas Ranger, and as Nicky in 1995's Casper.

Leopardi remained good friends with Sandlot co-star Patrick Renna, who was a '90s mainstay in his own right with gigs on The X Files, Home Improvement, and Boy Meets World. "[Chauncey's] the one guy that I hung out with for years to come," Renna said in a 2020 YouTube video with Leopardi on his channel, You're Killing Me, adding that in addition to their days on the dirt, the two did two additional sports movies together: 1995's soccer comedy The Big Green and 2001's "little-known" basketball film Boys Klub. "We need to do a hockey movie," Leopardi joked.

While most of his characters were comical big mouths, Chauncey Leopardi took a wicked turn as bully Alan White in 1999's cult series Freaks and Geeks. With his long hair and powerful pitches, Leopardi's character makes dodgeball a living hell for geek Sam Weir and his friends, although it's later revealed he's acting out of his own feelings of loneliness. The show, created by Paul Feig and executive produced by Judd Apatow, didn't last more than a season on network television, however it developed a devoted following over the years, helping launch the careers of Leopardi's co-stars Seth Rogen, James Franco, Jason Segel, and Busy Philipps.

Considering the show cultivated a fandom years past its premiere — much like The Sandlot, Leopardi is down for a reunion, although he told The Reel Place in 2013 that nothing was in the works. "I talk to Martin Starr here and there, but I haven't seen Seth [Rogen], [James] Franco or any of those guys since we pretty much worked on the show," he said. The majority of the show's cast later reunited for a 2013 Vanity Fair cover, however Leopardi did not participate for unknown reasons.

From 2003 to 2005, Chauncey Leopardi graced the charming neighborhood of Stars Hollow with a recurring role as Kyle Gibson on The WB's Gilmore Girls. As one of Jared Padalecki's character Dean's best friends, viewers saw Kyle transform from a partying high school teenager to a wounded Navy veteran with a hook for a hand. Don't worry, though, with his signature charm, he tells Rory (Alexis Bledel) that it's "a real chick magnet."

Though Leopardi was maturing in his 20's and his Gilmore Girls character was quite the Casanova, he told Patrick Renna on You're Killing Me that he didn't reap the benefits of his attractiveness and notoriety till later in the game. "My fame from that s**t didn't come until way, way later," he said. "I aged well." 

He portrayed a bad boy caught in a taco stand spat in a 2005 guest role on CSI before reportedly taking a break from acting for a few years.

Chauncey Leopardi delivered the following shocker to the Ya Neva Know podcast in 2019, admitting he "did everything fast," and revealing that he got married at 18-years-old and was a father by 21. According to TMZ, Leopardi and ex-wife Stefani married in 2000 and filed for divorce in 2013, however they had been separated since 2003 and had been "too lazy to file the docs." He shares one daughter, Paige, with his former wife, and he has another daughter Shia and a son, Chance.

Leopardi is currently unmarried, however he revealed on social media in 2020 that he was dating Los Angeles Rams cheerleader Jennifer Garcia, and introduced her to Patrick Renna during his You're Killing Me YouTube series. He seems to be taking fatherhood seriously, writing in an Instagram post on his son's second birthday, "I named you Chance because you're my second chance at life." 

As for his kids, they've all seen The Sandlot by now, though considering his youngest are children themselves, the jury's out on their official evaluations. "Their mom sent me a picture of them with their grandma sitting on the couch watching it," he told the San Antonio Current in 2018. "I think they were into it, so that's good."

Chauncey Leopardi touched home base again when he reprised his role as Squints in 2007's direct-to-video release The Sandlot: Heading Home, starring Luke Perry. Michael Palledorous, who still bears his signature glasses and backwards cap, has grown to become the town's baseball commissioner, as well as an optometrist. As the only original cast member to return to the franchise, he works alongside a grown-up Benny Rodriguez, portrayed by Danny Nucci in the film, to help a younger version of Perry's character whip a new group of sandlot players into shape. While Leopardi was initially against sequels, he told RobotBitesMan that he was "impressed" after reading the script, adding that "The Sandlot had been a really big part of my life so I figured I owed it Fox."

The film finds Squints helping lead the boys to victory in a baseball showdown against a group of real estate developers plotting to tear the sandlot down. They guaranteed the lot's survival, marking a full-circle moment for Leopardi, who appeared at a 2013 dedication ceremony honoring the original site in Salt Lake City, Utah, with a historical marker. According to Deseret News, it's the first plaque the Utah Film Commission ever granted.

What started out as an internet meme led to a high-profile gig for Chauncey Leopardi in 2019. When the viral 10 Year Challenge comparing new and old pics spread on social media, rapper Logic used a photo of Squints as his younger self, with Leopardi signing off on the likeness by reposting it himself. Later that year, he received an offer to play himself in Logic and Eminem's video for "Homicide." The visual finds Leopardi scoring the role of impersonating Logic, playing on their similarities to act as a stand-in when Eminem is unable to make the shoot and plans to use Chris D'Elia as his body double (via Stereogum).

While Logic was unaware that Leopardi, a hip-hop fan, would be able to spit rhymes as well as he did, the actor told The Mystery Hour that it was "one of those perfect synchronicities in life," and he thinks he left the rapper impressed. Although Leopardi admits he was very eager and superstitious about the booking, telling his agent to, "Play it cool (...) but don't mess this up."

While the boys of The Sandlot couldn't handle the mix of chewing tobacco and carnival rides in the film, that hasn't stopped Chauncey Leopardi from indulging as an adult. The L.A. actor is very open about his cannabis use on social media, creating his own marijuana company "Squintz," featuring a slightly blazed caricature of his trademark character on the logo, complete with red eyes, glasses and baseball cap. According to Visit Hollyweed, his products are available in California and include a self-named strain. 

In 2020, Leopardi took his advocacy for the recreational drug one step further and created his own podcast, Picture Me Rolling, highlighting "his love of cannabis." The actor, father, and entrepreneur seems to keep his passions separate and rarely discusses his work with marijuana in interviews. He continues to be an outspoken voice for drug reform, using his platform to raise awareness about The Weldon Project's MISSION [GREEN] initiative, which seeks to fund "social change and financial aid" for those "serving prison time for cannabis-related offenses." Leopardi called it a "great cause" on Instagram, adding that "drug reform is one of the most important discussions in our society today."

Chauncey Leopardi hardly expected that he'd still be recognized for a role he played as a child, but he told Texas Standard that the film's generational impact is really "humbling." As the cast continues to reunite over the years to celebrate its milestone anniversaries, the actor revealed to the San Antonio Current that it feels like "getting together with family." Still, considering its meager box office performance and mixed reviews upon release, no one could've predicted the coming-of-age story would stand the test of time.

"Everyone thought it was a cool film, good piece, but nobody really saw it," Leopardi told the Green Bay Press Gazette. But because of its setting "in this time lapse of ... this summer in 1962," he believes it's something audiences "will always be able to go back [to] ... and say it's classic Americana." It seems that Leopardi has no problem going down in history as Squints; not only did he name his marijuana brand after the character, but he regularly shares shots of epic Sandlot-inspired tattoos on Instagram.

For the most part, Chauncey Leopardi no longer acts after his last role in the 2013 indie film Coldwater, however he'd reportedly "consider a return for the right opportunity" (via Green Bay Press Gazette). That opportunity might be coming sooner than later, though, as Variety reported in 2019 that Disney Plus was developing a spinoff series focusing on the original cast's children in the '80s. Ham himself, Patrick Renna, seemed to confirm the project was in the works in a 2020 interview with ET Canada, adding that they were "brought to a studio in Hollywood about a year ago ... and everyone was pretty much into it."

Considering Leopardi's love for his character, we would not be surprised to see Squints don the glasses once more. After all, he's had no problem wearing them for the franchise's third film, and he understands their power after all this time. "The effect of Squints is missed without the glasses," he said in 2019's YouTube documentary The Sandlot Forever. "I put 'em on for the fans ... because just seeing me with the glasses and the hat makes it all different." Considering how well-rounded — and good-looking — Leopardi's grown up to be, it's safe to say the spectacles are definitely doing things for all of us.