Caan followed his first major studio films, Enemy of the State (1998) and Varsity Blues (1999) with macho roles in male-oriented fare such as Boiler Room and Gone in 60 Seconds (both 2000). He subsequently landed a recurring gig as Casey Affleck's other half in the star-studded Ocean's Eleven franchise.
In 2005, Caan made his directorial debut while also playing the title role in Dallas 362. Five years later, he joined the cast of the reimagined "Hawaii Five-O" in the iconic role of Danny "Danno" Williams, earning his first Golden Globe nomination.