His break came when he was cast as Sergeant Brad "Iceman" Colbert in the critically acclaimed HBO miniseries Generation Kill.
An adaptation of journalist Evan Wright's book of the same name, Generation Kill follows the 1st Reconnaissance Battalion of the United States Marine Corps during the early part of the Iraq War.
Grace played a prep school student who uses marijuana and introduces his girlfriend to freebasing in director Steven Soderbergh's 2000 film Traffic, as well as having uncredited cameos as himself in Soderbergh's Ocean's Eleven and its 2004 sequel, Ocean's Twelve.
"The joke is that you're supposed to play the worst version of yourself and I don't think too many people are comfortable with that.
At first he was unsure about playing a vampire, but when he learned that Alan Ball, creator of the HBO series Six Feet Under and Academy Award winning screenwriter of American Beauty, was behind the project, he sent in an audition tape.
The audition was for the role of Bill Compton, which eventually went to Stephen Moyer.
I never thought for a second that people were really going to think that's what I was like.
I think that people will know that I was faking it in those movies," he told Flaunt magazine in 2007. However, due to his role in Spider-Man 3, he had to abandon these plans. S., which received only a limited theatrical release.
The film co-starred James Marsden and Kate Bosworth Skarsgård was the Ambassador for the American team for a Walking With The Wounded fundraising event for wounded soldiers.As Grace said, "I was doing reshoots on Spider-Man 3. I actually talked to Steven Soderbergh about that and we had a thing and then I couldn’t do it." In 2004, Grace played the leading roles in Win a Date with Tad Hamilton! Grace won the National Board of Review's 2004 award for Breakthrough Performance Actor for his work in In Good Company and P. In 2012, Grace starred alongside Mary Elizabeth Winstead and Matthew Gray Gubler in the social film The Beauty Inside, which won a Daytime Emmy Award for Outstanding New Approach to an Original Daytime Program or Series in 2013.The film was directed by Drake Doremus and written by Richard Greenberg.Grace played Mike Smith, a researcher on the story.In January 2014, Grace joined the upcoming supernatural-thriller Delirium, which centers on a man recently released from a mental institute who inherits a mansion after his parents die.The role of Brad Colbert was the closest to a "lead" in Generation Kill, and director Susanna White and executive producer David Simon at first disagreed about casting Skarsgård.White wanted to cast him but Simon was not convinced he could pull off the American accent.That same year, he co-starred in Truth, with Robert Redford and Cate Blanchett, and based on the story of CBS's 60 Minutes report that George W.Bush had received preferential treatment to keep him out of the Vietnam War.Uncomfortable with being recognized, he quit acting for the next seven years.After completing his service in 1996 he left Sweden and attended Leeds Beckett University in England for six months.