Damon's attempts at essaying leading characters in romantic dramas such as 2000's All the Pretty Horses and The Legend of Bagger Vance were commercially and critically unsuccessful.
Upaya Damon menjadi karakter-karakter utama dalam film drama romantis seperti dalam All the Pretty Horses dan The Legend of Bagger Vance ternyata mendapatkan kegagalan komersial dan kritikan.