Dawson Casting: A strange case. Frank James, Jesse's older brother, is 38. It's implied that his life as a bandit has been hard on his looks, so maybe he's supposed to look about 50. He was played by Sam Shepard, aged 64 at the time. The 32-year-old Casey Affleck also plays Bob from the age of 20, though the film follows him through the rest of his life. Brad Pitt is also nine years older than Jesse was at the time of his death.