Supernatural (2005)

S5E7 The Curious Case of Dean Winchester

Sam and Dean stumble upon a witch hosting a dangerous poker game where participants wager years of their lives instead of cash. Bobby sees this as an opportunity to regain his mobility and risks 25 years, but unfortunately, he loses the bet. As Bobby starts to age at an alarming rate, Dean rushes to his aid, only to find himself transformed into an elderly man. This leaves Sam to navigate their perilous situation alone as he must find a way to save them both.