# Chauncey Leopardi
**Chauncey Leopardi** (born 1981) is an American actor best known for playing Michael "Squints" Palledorous in the 1993 family baseball comedy *The Sandlot*, a role he reprised as an adult in the 2007 direct-to-video sequel *The Sandlot: Heading Home*.[1](https://www.rottentomatoes.com/celebrity/chauncey_leopardi) • [2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/) A working child actor through the 1990s, he later took recurring television roles as the bully Alan White on *Freaks and Geeks* and as Kyle on *Gilmore Girls*, before his screen work thinned out in adulthood.[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/)
| Key fact | Detail |
|---|---|
| Signature role | Michael "Squints" Palledorous in *The Sandlot* (1993), the bespectacled kid who fakes drowning to get a kiss from lifeguard Wendy Peffercorn[1](https://www.rottentomatoes.com/celebrity/chauncey_leopardi) • [3](https://www.thereelplace.com/news/the-sandlot-interview-chauncey-squints-leopardi/) |
| Born | 1981[1](https://www.rottentomatoes.com/celebrity/chauncey_leopardi) |
| Other 1990s films | *Father of the Bride* (1991), *Casper* (1995), *Houseguest* (1995), *Safe* (1995), *The Big Green* (1995)[1](https://www.rottentomatoes.com/celebrity/chauncey_leopardi) |
| Television | Alan White on *Freaks and Geeks* (1999); Kyle in five episodes of *Gilmore Girls* (Seasons 3, 4, and 5)[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/) |
| Sequel return | Reprised Squints as an adult in *The Sandlot: Heading Home* (2007), the only member of the original cast to do so[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/) |
| Career span | Active from about 1990, with only a smattering of credits after 2007[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/) |
## The Sandlot and Squints
*The Sandlot*, released April 7, 1993, follows a group of small-town kids playing summer baseball at a rundown diamond they call the sandlot, where newcomer Scotty Smalls loses a ball signed by [Babe Ruth](https://www.edgepedia.org/babe-ruth) over the fence of a yard guarded by a huge attack dog known as The Beast.[4](https://www.thewrap.com/sandlot-anniversary-90s-baseball-cult-classic-chauncey-leopardi/) Leopardi's Squints became one of the film's most quoted characters: he tells the story of the Beast with the refrain "for-ev-ver," and his staged drowning to steal a mouth-to-mouth kiss from lifeguard Wendy Peffercorn ([Marley Shelton](https://www.edgepedia.org/marley-shelton)) remains a fan-favorite scene.[3](https://www.thereelplace.com/news/the-sandlot-interview-chauncey-squints-leopardi/) • [2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/)
**Casting.** Leopardi originally read for the part of Yeah-Yeah and was upset when director David Mickey Evans asked him to read for Squints instead; Evans repeatedly reshuffled young actors among the roles until the personalities fit.[5](https://baseballhistory.org/articles/the-sandlot-and-the-summer-that-wasnt) The film was shot in Utah during the summer of 1992, set in the [San Fernando Valley](https://www.edgepedia.org/san-fernando-valley) in 1962.[4](https://www.thewrap.com/sandlot-anniversary-90s-baseball-cult-classic-chauncey-leopardi/) • [5](https://baseballhistory.org/articles/the-sandlot-and-the-summer-that-wasnt)
The film's afterlife has kept Leopardi connected to the role. In 2013 he joined Evans and co-star [Patrick Renna](https://www.edgepedia.org/patrick-renna) at [Boston Red Sox](https://www.edgepedia.org/boston-red-sox) batting practice, where [David Ortiz](https://www.edgepedia.org/david-ortiz) greeted them as his heroes, and at 2018 spring training the Milwaukee Brewers re-enacted a famous scene from the film.[4](https://www.thewrap.com/sandlot-anniversary-90s-baseball-cult-classic-chauncey-leopardi/) He regularly appears with castmates at reunions and convention appearances.[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/)
## Child actor of the 1990s
Leopardi began performing young. He first appeared on television in 1990 in a series of commercials at about age six, after a talent agency recruited him when he accompanied his cousin to a meeting; a year later he moved to Los Angeles with his mother and landed roles in commercials, television series such as *Christine Cromwell* and *L.A. Law*, and films including *Father of the Bride* and *A Girl of the Limberlost*.[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/)
Work stayed steady through the rest of the decade. In 1995 alone he appeared in three releases: as Nicky, one of two youngsters exploring Whipstaff Manor in the opening scene of the ghost comedy *Casper*; as Jason Young, the 11-year-old son of [Phil Hartman](https://www.edgepedia.org/phil-hartman)'s character in the Sinbad comedy *Houseguest*; and as Rory in the psychological horror film *Safe*, set in a town where [Julianne Moore](https://www.edgepedia.org/julianne-moore)'s character becomes mysteriously ill.[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/) His credits also include *The Big Green* (1995), *The Paper Brigade* (1996), *Trojan War* (1997), and *The Opposite of Sex* (1998).[1](https://www.rottentomatoes.com/celebrity/chauncey_leopardi)
## Freaks and Geeks and Gilmore Girls
As film roles became less frequent at the end of the 1990s, Leopardi moved largely to television. On the NBC series *Freaks and Geeks*, an early project of executive producer [Judd Apatow](https://www.edgepedia.org/judd-apatow) set at the fictional William McKinley High School in Michigan, he played Alan White, a recurring bully to the geeks Sam Weir ([John Francis Daley](https://www.edgepedia.org/john-francis-daley)), Neal Schweiber ([Samm Levine](https://www.edgepedia.org/samm-levine)), and Bill Haverchuck (Martin Starr).[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/) Introduced in the pilot as Sam's nemesis, Alan ends his feud with the geeks after one of his pranks lands Bill in the hospital, and the two bond as a result.[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/) The show, which premiered in September 1999, was canceled after only a dozen episodes had aired but is widely regarded as a cult classic.[6](https://www.washingtonpost.com/arts-entertainment/2021/01/27/freaks-and-geeks-streaming-hulu-cast-creators-interview/)
A few years later Leopardi joined *Gilmore Girls* on The WB, appearing in five episodes across Seasons 3, 4, and 5 as Kyle, a Stars Hollow High School student and friend of Dean Forester ([Jared Padalecki](https://www.edgepedia.org/jared-padalecki)). Kyle hosts the party at which Jess and Rory argue and break up, then leaves to join the Navy, returning for Dean's bachelor party with a hook replacing a missing hand; Dean later moves in with him.[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/)
## Later career
By the 2000s, roles dried up as Leopardi aged out of child parts. He had one-off guest appearances in *Snoops*, *Walker, Texas Ranger*, and a 2005 episode of *CSI: Crime Scene Investigation*, and joined the cast of the 2001 family comedy *Boys Klub*.[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/) In 2007 he returned to the franchise that made his name, playing an older Squints in *The Sandlot: Heading Home*, the only member of the original cast to appear in the time-travel sequel.[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/)
He effectively stepped back from acting by the early 2010s, with only a smattering of credits after 2007. In a 2008 interview he said he had "taken a break from the acting game for a while" and was working on his own material, including sketch comedy posted online, some of it on [Funny or Die](https://www.edgepedia.org/funny-or-die); he has suggested he would return to acting for the right role.[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/) In interviews he has noted that he stayed in touch with few former co-stars outside *The Sandlot* reunions, speaking occasionally with [Martin Starr](https://www.edgepedia.org/martin-starr) but not seeing [Seth Rogen](https://www.edgepedia.org/seth-rogen) or James Franco since the *Freaks and Geeks* shoot, and losing contact with Marley Shelton for more than two decades before reconnecting in recent years.[2](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/)
## References
1. [Chauncey Leopardi, Rotten Tomatoes celebrity page](https://www.rottentomatoes.com/celebrity/chauncey_leopardi)
2. [Whatever Happened To Squints From The Sandlot?, Looper (Nathan P. Gibson, December 10, 2023)](https://www.looper.com/1465554/squints-sandlot-chauncey-leopardi-child-star-whatever-happened-to-him/)
3. [The Sandlot Interview: Chauncey "Squints" Leopardi, The Reel Place (Luke Hickman, July 24, 2013)](https://www.thereelplace.com/news/the-sandlot-interview-chauncey-squints-leopardi/)
4. [The Sandlot: Why the '90s Cult Classic Will Live 'For-Ev-Ver', TheWrap (Brian Welk, April 7, 2021)](https://www.thewrap.com/sandlot-anniversary-90s-baseball-cult-classic-chauncey-leopardi/)
5. [The Sandlot and the Summer That Wasn't, Baseball History](https://baseballhistory.org/articles/the-sandlot-and-the-summer-that-wasnt)
6. [How 'Freaks and Geeks' went from misfit dramedy to cult classic, The Washington Post (Sonia Rao, January 27, 2021)](https://www.washingtonpost.com/arts-entertainment/2021/01/27/freaks-and-geeks-streaming-hulu-cast-creators-interview/)
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*Topic: Encyclopedia › Arts and culture › Screen and stage › Film and television › Screen people and creators › Screen actors of the Anglosphere and Europe › American actors: 1970s to 1990s › Surnames Le to L*
*Initially written Sep 17, 2026 · Reviewed: Sep 17, 2026; Sep 20, 2026; Sep 30, 2026; Oct 25, 2026 · Edited: Sep 20, 2026; Sep 30, 2026; Oct 12, 2026; Oct 15, 2026; Oct 25, 2026 · Last review: Oct 25, 2026*
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