1995–2004: Career beginnings After making an uncredited appearance in
Baywatch in 1995, followed by filming a cameo in the film
Mercenary in 1996, Pressly starred as Violet, a vengeful seductress, in the 1997 direct-to-DVD film
Poison Ivy: The New Seduction, the third installment of the
Poison Ivy series. After a small role in the teen cult classic ''Can't Hardly Wait
, television appearances followed, with guest roles in the short-lived Push and Mortal Kombat: Conquest. She went on to play one of the leads in Jack & Jill, which aired for two seasons, from September 26, 1999, to April 15, 2001, on The WB. Pressly headlined the independent film Poor White Trash (2000), playing scheming gold-digger Sandy Lake, and appeared in three 2001 theatrical releases aimed at a teenage audience, which despite varying degrees of success, helped her receive more exposure. The parody film Not Another Teen Movie, most notably, featured her as Priscilla, a high school cheerleader opposite Chris Evans, while she took on the roles of a young wife in the sex comedy Tomcats and that of a Southern love interest in the comedy Joe Dirt'', opposite
David Spade. In 2002, Pressly starred as a college student trapped in a haunted island in the independent horror film
Demon Island. Felix Vasquez of
Cinema Crazed regarded it as a guilty pleasure and stated: "[She] does what she can with her character and comes off as a rather charming character". She next portrayed a crazed, motorcycle-riding criminal in the action thriller
Torque (2004), alongside
Ice Cube. In a profile,
The New Yorker, describing this phase of her career, asserted: "She is typically cast on the strength of her looks and her Southern sassiness, and she has had girlfriend roles in several forgettable teensploitation flicks".
2005–2009: Breakthrough '' in 2009 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
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".
2010–present: continued television roles The
ABC Family television film
Beauty & the Briefcase (2010), co-starring
Hilary Duff, featured Pressly as a primary editor at
Cosmopolitan magazine. The premiere received 2.4 million viewers attracting a strong female audience that drove the network to an all-time high in viewers.
Smoke Screen, another 2010 television film, saw her star as a reporter finding herself in the middle of a murder investigation when she wakes up next to a dead body. In 2010, Pressly also guest-starred in two episodes of the
CBS comedy
Rules of Engagement, as a possible surrogate mother for Jeff and Audrey (
Patrick Warburton and
Megyn Price). In
6 Month Rule (2011), an independent film released for limited theaters and digital markets, Pressly played what was described as a "harridan of an ex-fiancée" by the
New York Times. She appeared in the
interactive educational
children's musical comedy
The Oogieloves in the Big Balloon Adventure (2012), as a flamenco dancer riding a giant flying sombrero. Budgeted at US$20 million, the film only made US$445,000 in more than 2,000 screens during its opening weekend. Pressly next had regular roles in two short-lived series. The
Fox sitcom
I Hate My Teenage Daughter (2011–2012) saw her portray a mother fearing her daughter is turning into the kind of girl who tormented her in high school, while the
TV Land comedy
Jennifer Falls (2014) featured her as a single mother, who after being fired from a high-paying job, becomes a waitress in her brother's bar. Pressly obtained leading roles in three 2014 film releases. In
A Haunted House 2, Pressly starred as a mother of two and one half of an interracial couple, alongside
Marlon Wayans. She had known Wayans for 15 years prior filming and the project marked the first time they worked together. Describing the process, she said: "It was a match made in heaven. It really was. We're both high energy, and we both like to do something new every take, and when you do comedy like this, where you get to improv the majority of the time, it's about trying to one-up each other, and that makes for a really great comedy". The film was panned by critics, but was a decent box office success. She starred opposite singer
Robin Thicke in the romantic comedy
Making the Rules, which was filmed in 2012.
Finders Keepers, a television horror film, saw Pressly play a divorced mother whose life is thrown into turmoil when her young daughter becomes obsessed with an evil doll left behind by the previous owners. From 2014 to 2021, Pressly portrayed Jill Kendall, a wealthy socialite and alcoholic, in the
CBS sitcom
Mom.
Mom was met with widespread critical acclaim and ran for eight seasons. Created and executive produced by
Chuck Lorre, the show followed a group of women recovering from addiction. == Other ventures ==