Billing Displacement: Sigourney Weaver is billed first, and yet does not appear until forty minutes into the film. Jon Voight and Patricia Arquette are billed second and third, despite just playing supporting characters. Shia LeBeouf was then only known for the sitcom Even Stevens.
Black Sheep Hit: The film was this for director Andrew Davis. He is best known for directing action-thriller type films (such as Under Siege and The Fugitive). Holes, in comparison, is more of a family-adventure type film. It is also only the second PG rated film he has directed (the first, Stoney Island, was made before he gained considerable commercial success while his other films are either rated PG-13 or R). Regardless, the film was well received critically and was successful at the box office, earning $71 million on a $20 million budget.
Breakthrough Hit: The novel is one for Louis Sachar. It's quite different than his previous work, being a darker and more dramatic novel aimed at an older audience than most of his other works, which are typically lighthearted and absurdist (such as the Wayside School series). It ended up being Sachar's first Newbery Medal winner, and remains one of his most well-known novels.
California Doubling: The film was shot entirely in California, even the scenes that were set in Texas.
Fake American: The presumably American Clyde "Sweet Feet" Livingston is played by Canadian actor Rick Fox.
Hostility on the Set: During filming, Shia LaBeouf's father and on-set guardian Jeffrey frequently tried hitting on Sigourney Weaver, which made her very uncomfortable.
In Memoriam: The film is dedicated to Scott Plank (Trout Walker's actor), who died in a car accident in October 2002.
Irony as She Is Cast: While Clyde "Sweet Feet" Livingston is a baseball player, his actor Rick Fox was a basketball player at the time of the film's production.
Permanent Placeholder: When Louis Sachar was writing the book, he used Stanley Yelnats as a filler name for the main character, planning to replace it later with a more normal name. He never did, and the weird name even ended up becoming a plot point.
Posthumous Credit: Although Scott Plank was killed in a car crash in October 2002, six months before the film's release, he's still credited for his work as Trout Walker.
Promoted Fanboy: The cast commentary features four of the D-tent boys gushing over most of their adult co-stars, particularly Sigourney Weaver and Eartha Kitt. Khleo Thomas in a The Tiara Talk Show podcast interviewnote mentioned at time stamp 9:08 also mentions being a fan of Weaver since Ellen Ripley and he blurted out in shock seeing her as none of the boys knew she'd been cast as the Warden until they saw her in wardrobe on set.
Real-Life Relative: Nathan Davis, the actor who played Stanley Yelnats II (Stanley's grandfather), was director Andrew Davis' father. Another relative was also used in the jail sequence where Kathryn returns to the sheriff's office and becomes Kissin' Kate Barlow.
Referenced by...: JoJo's Bizarre Adventure: Stone Ocean has a villainous character named Donatello Versus, whose backstory is nearly identical to Stanley's, being arrested and sentenced for theft of a pair of shoes after it landed on his head. The only differences between Versus and Stanley in this respect is that Versus' prison is much worse and doesn't involve an ancient family curse (well, not on his family anyway).
Self-Adaptation: Louis Sachar wrote the screenplay for the film. His draft almost wasn't used, but ultimately retained, and skewed far closer to the book than the other optioned draft. Only minimal edits were made, most of which were fixing minor plot holes present in the book.
Throw It In!: During the scene where Mr. Sir brings Stanley to the Warden's cabin, Jon Voight adlibbed the speech about how Mr. Sir keeps the campers in line.
Frankie Muniz was the first choice to play Stanley in the film.
An early draft of the novel had a whole chapter that was nothing but the word "dig" written over and over again for five pages before ending with the word "spit".
Richard Kelly was offered the chance to do this movie. He was replaced when they saw his screenplay, which was nothing like the book. It was set in a post-apocalyptic Crapsack World where Stanley's crime was Mercy Killing his plague-infected sister instead of stealing a pair of shoes. And instead of a bandit's stash of money, the "buried treasure" that Stanley found was going to be a long-lost Weapon of Mass Destruction. It also features a character uttering the phrase 'big titty slut'. You can find the script here (NSFW, obviously).
Kissin' Kate's signature Kiss of Death was originally going to be to wear lipstick made from rattlesnake venom. This was later changed to be the Warden's nail polish.
Shia LaBeouf originally decided to put on weight to match Stanley's overweight build from the novel. However, this idea was shot down by the director, who pointed out that to gain and lose that much weight in a short span of time would be dangerous for someone of LaBeouf's age at the time (weight fluctuation, in general, is a considerable heath risk). Louis Sachar himself ended up telling LaBeouf that it was more important to focus on Stanley's personality than his appearance.
note also mentions being a fan of Weaver since Ellen Ripley and he blurted out in shock seeing her as none of the boys knew she'd been cast as the Warden until they saw her in wardrobe on set.