Woodward's first on-screen acting job came in 1991 when she played the occasionally recurring role of Missy on Nickelodeon's television seriesClarissa Explains It All. She reprised this role twice during the show's five seasons. Woodward next appeared in made-for-television films: ' and Tornado!. In 1997, she played an uncredited role in the CBS miniseries True Women. Between 2000 and 2007, Woodward played a number of minor roles in various television shows including The Drew Carey Show, Grounded for Life, Malcolm in the Middle, Crossing Jordan, Without a Trace, Psych, and Boston Public. Woodward's big-screen debut came in 2005 when she played Emma Sharp, the daughter of a Texas Ranger assigned to protect a group of cheerleaders who witnessed a murder in the action comedy Man of the House. In 2007, Woodward got her big break in the series The Riches, which aired for two seasons on cable network FX. She played the role of Di Di Malloy, the teen daughter and middle child in an American family of Irish Travellers. After The Riches ended, Woodward played the role of Leah in the film The Haunting of Molly Hartley. Woodward shot the 2009 pilotLimelight, about a New York City school for performing arts, but the series was not picked up. That same year, Woodward had a recurring role on the final season of NBC's ER, as Kelly Taggart, the younger sister of nurse Samantha "Sam" Taggart. She also starred in another teen thriller, The Shortcut. In 2010, Woodward starred in the independent drama Girlfriend. She also played the lead character in the 2015 ensemble comedy-drama The Breakup Girl. From September 2010 to April 2014 Woodward had a starring role in the FOX sitcom Raising Hope, playing Sabrina Collins, a grocery store checkout clerk who is the love interest of the series lead. Woodward appeared in her friend Katy Perry's music video "Hot n Cold" and had a cameo role in Perry's documentary/concert film '. Perry, in turn, guest-starred in a season two episode of Raising Hope. Woodward played Lois in the 2017 film All Nighter., she is in her second season as computer programmer Elsie Hughes, in a regular role on the HBO series Westworld. It was announced in April 2017 that Woodward will appear in The Last of UsPart II.