He won the Satellite Award for Best Actor – Motion Picture for Running with Scissors (2006), and co-starred in Flags of Our Fathers (2006), Untraceable (2008), Milk (2008), and Lincoln (2012).
He subsequently appeared in several television roles, notably portraying Casey Hughes in the CBS daytime soap opera As the World Turns (1999–2004).
In 2006, Cross played the young Augusten Burroughs in Running with Scissors, a drama also featuring Annette Bening and Evan Rachel Wood, and appeared as real-life Marine Franklin Sousley in the big-budget Flags of Our Fathers, a Clint Eastwood-directed war film.
The following year, he played William "Fred" Parsons in the West End production of Breakfast at Tiffany's, at the Theatre Royal Haymarket, opposite Anna Friel.
[9] He portrayed the lead role of Davis Green in the drama film The Automatic Hate (2015), alongside Deborah Ann Woll.