
Ulrich and Cates separated in 2004 and filed for divorce in 2005, citing irreconcilable differences. They have twins, Naiia (daughter) and Jakob (son), born in 2001. Their wedding was a small ceremony held on their farmland in Madison County, Virginia, with only the preacher and their canine companions as guests. In 1997, Ulrich married English actress Georgina Cates, whom he met at an Academy Awards party. In 2022, Ulrich reprised his 1996 breakout role as Billy Loomis from Scream in the 2022 sequel of the same name, the fifth film in the franchise.
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He also played Brice in the 2017 horror movie Escape Room. Ulrich appeared as Brian David Mitchell in the 2017 Lifetime film I Am Elizabeth Smart, based on the 2002 abduction and captivity of Elizabeth Smart. From 2017 to 2021, he starred as Forsythe Pendleton Jones II, the father of Jughead Jones, in Riverdale on The CW, loosely based on the Archie comic book series. Ulrich guest-starred in three episodes of CSI: NY as a complex and disturbed killer.
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Ulrich is a recurring guest voice actor on the Adult Swim animated stop-motion sketch comedy series Robot Chicken. Fans lobbied the studio, and the series was brought back for a shorted second season. The series was cancelled after its first season but was brought back due to fan outcry and support. He starred as Jake Green on the CBS post-apocalyptic drama Jericho, which premiered on September 20, 2006, and ended its run on March 25, 2008. Also in 2005, Ulrich acted with Keri Russell in the television film The Magic of Ordinary Days. On television, Ulrich starred in the short-lived ABC series Miracles and appeared in TNT's multiple Emmy-nominated miniseries Into the West (2005 in the U.S., 2006 in the UK). In 2000, he played computer hacker Kevin Mitnick in the film Takedown.

He starred as Juvenal, a young man with stigmata and healing powers in the Paul Schrader film Touch (1997), and he appeared in Ride with the Devil (1999), an American Civil War drama directed by Ang Lee. He appeared in films like The Newton Boys (1998) and Chill Factor (1999). In 1997, he had a small role as an emotionally conflicted gay hustler in As Good as It Gets (along with fellow Scream actor Jamie Kennedy). He was cast that same year to star alongside Campbell again in Wes Craven's hit slasher film Scream as Billy Loomis. That same year, he also appeared in Kevin Spacey’s directorial debut Albino Alligator and The Craft alongside Robin Tunney and Neve Campbell. With her help, he also received his first notable role on screen in 1996 as the loutish boyfriend of Winona Ryder in Boys. She cast him in a CBS Schoolbreak Special. After joining the Atlantic Theater Company as an apprentice, Ulrich performed with the group, which got him noticed by director Stacy Cochran. In his earliest screen appearances, Ulrich was an uncredited extra in films Weekend at Bernie's (1989) and Teenage Mutant Ninja Turtles (1990). After enrolling at the University of North Carolina at Wilmington to study marine biology, he switched to New York University, where he was noticed by playwright David Mamet. Ulrich graduated from Northwest Cabarrus High School in North Carolina. Along with his slight frame, he had poor health, including numerous bouts with pneumonia he underwent open-heart surgery to repair a defective ventricle at the age of 10. The nickname "Skeet" originated from "Skeeter", a nickname he was given by his Little League coach because of his small stature and because he was fast as a mosquito. They were reunited with their mother in North Carolina, where his father disappeared from his life.

Ulrich's father kidnapped him and his brother when he was six years old, and they spent the next three years moving from Florida to New York and then to Pennsylvania.

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Ulrich's maternal uncle is retired NASCAR driver Ricky Rudd, and his maternal grandfather was Alvin Ray Rudd, Sr., the president of Al Rudd Auto Parts. In 1990, his mother remarried, to Edward Lewis Wax. Ulrich, a NASCAR driver and team owner, whom he considers his father. His mother, Carolyn Elaine Wax ( née Rudd), owns the special events marketing agency Sports Management Group, and his father is a restaurateur. Bryan Ray Trout was born on January 20, 1970, in Lynchburg, Virginia.
