The Road So Far: A Milestone Look at "Point of No Return" Supernatural ’s 100th episode, (Season 5, Episode 18), is more than just a numerical milestone; it is the definitive tipping point for the series' original five-year arc. Originally aired on April 15, 2010, and written by Jeremy Carver , this episode strips the Winchester brothers down to their rawest nerves before forging a new, defiant path forward. The Weight of the World: Dean’s Darkest Hour
In a devastating moment, Dean tells a pleading Bobby Singer , "You’re not my father," prompting Bobby to reveal the single bullet he considers using on himself every morning. [S5E18] Point of No Return
Dean’s despair leads to some of the show’s most painful character interactions: The Road So Far: A Milestone Look at
The episode opens with at his absolute breaking point. Convinced that saying "yes" to the Archangel Michael is the only way to stop Lucifer , he begins settling his affairs—packing away his leather jacket and the keys to the Impala . Dean’s despair leads to some of the show’s
Castiel , who rebelled against Heaven for Dean, reaches his limit. After Dean tries to trick him with an angel-banishing sigil, Cas delivers a brutal physical beatdown, shouting that he didn't give up everything only to watch Dean "fail". The Return of the Third Brother Supernatural: "Point of No Return" - AV Club