Michael Clayton 2007
Gilroy's first film as director, born from a law-firm research trip for 'Devil's Advocate,' where he noticed the real work happened behind the empty wood-paneled conference rooms. Clooney as a mid-level fixer at a Manhattan firm, $80,000 in debt from a failed restaurant, cleaning up a billion-dollar case built on a 'bad document' modeled on a real 1973 GM memo that found it cheaper to pay death benefits than fix cars that were catching fire. Clooney waived his fee to get it made and Gilroy took no money either. It made $50M and won Tilda Swinton an Oscar. The two-minute closing shot on Clooney's face in the back of a cab came together at the last minute, over studio pushback for a happier ending.