Ashlee Simpson to star in 'Chicago' at Hollywood Bowl Ashlee Simpson, shown in 2005 on MTV's "Total Request Live" in New York, will portray Roxie in the musical "Chicago" at the Hollywood Bowl in late July. Peter Kramer / Getty Images July 8, 2013, 2:23 p.m. Ashlee Simpson -- pop star, reality TV veteran and younger sister to uber-celebrity Jessica Simpson -- will play the role of Roxie Hart in the production of the musical "Chicago" at the Hollywood Bowl this month.