2005–2009: Breakthrough
Between 2005 and 2009, Pressly played Joy Turner, the pessimistic, cold-hearted, stubborn and vain ex-wife of a small-time thief, in the NBC sitcom My Name Is Earl, which was a success with critics and audiences. She garnered nominations for a Golden Globe and a Screen Actors Guild Award, and in 2007, she won a Primetime Emmy Award for Outstanding Supporting Actress in a Comedy Series for her work on the show. Pressly once called her role her "greatest release" and thanked creator Greg Garcia for restoring her faith in the business. She remarked: "[The series] came at a time when I was questioning whether this was the path I wanted to continue following. I was tired of living out of my suitcase, coming and going all the time. I wanted a little normalcy in my life."
During the early run of My Name Is Earl, Pressly produced and took on the role of a homicidal magazine editor in the independent film Death to the Supermodels (2005), a role she compared to that of Reese Witherspoon in Election. In his review for the film, Scott Weinberg of DVDTalk.com, wrote: "Jaime Pressly is a funny, funny woman. To those of you My Name Is Earl fans who are just now discovering the juicy talents of the perpetually sneering, eye-rolling, attitude machine known as Jaime Pressly, I'd recommend you check out her work in flicks like Ringmaster, Tomcats, Joe Dirt, Torque, and Not Another Teen Movie. Basically, if we were giving out an award for "the consistently best thing in a series of generally atrocious comedies," Jaime would be walking home with that prize, no sweat. Regardless of how bad the movie is [...] Jaime always seems like a kooky and kinetic cartoon character who somehow figured out how to become flesh & blood. Yes, she's sexy and all that, but Jaime Pressly is also funny, and that just amplifies all her other assets".
In DOA: Dead or Alive (2006), a British-German martial arts action film based on a Japanese video game franchise of the same name, Pressly starred as one of four female fighters working together to uncover the secret that the organizer of an invitational martial arts contest is trying to hide. While the film was relatively successful on some markets, it only found a limited audience in North America. In 2006, she also hosted the first annual VH1 Rock Honors, and an episode of Saturday Night Live, and guest-starred on MADtv, playing Hillary Clinton in a parody of My Name Is Earl, "My Name Is Dubya", in which George W. Bush (Frank Caliendo) makes a list of all the bad things he has done in the past and rectifies them one by one. She voiced a bird in the animated comedy film Horton Hears a Who! (2008).
In I Love You, Man (2009), Pressly starred opposite Paul Rudd and Jason Segel, as the best friend of a bride-to-be and one half of a volatile married couple. The film received critical acclaim and was a box office success, grossing US$92 million worldwide. Rolling Stone found her "terrific" in her role, asserting: "Her battles with [her on-screen husband] have genuine comic bite".
