Supernatural produced its fair share of heartbreaking episodes over its first eleven seasons, and the Winchester boys have been through the emotional wringer on multiple planes of existence. Star Jared Padalecki has come out and revealed which episode to date was the roughest for him to film, and fans may be surprised to discover his pick. According to Padalecki, Season 3's darkly comedic Groundhog Day-esque "Mystery Spot" took the greatest toll on him. Padalecki had this to say about working on "Mystery Spot" back in 2008:
Back when "Mystery Spot" aired in Season 3, Supernatural hadn't yet fallen into the habit of killing and then resurrecting the Winchester boys on a semi-regular basis. Sam had died once, and Dean was counting down the days before he'd be killed by hellhounds and damned to hell, but Dean hadn't yet gotten a big death scene. It came as a shock in "Mystery Spot" when Dean took a shotgun blast to the chest. Dean went from waking Sam up by blasting "Heat of the Moment" on the radio to dead in a manner of minutes.
For a lot of us, that shock turned into amusement when the episode began a cycle of killing off Dean in increasingly ridiculous ways as Sam was stuck repeating the same Tuesday over and over again. Sure, it was gruesome to see Dean hit by a car and crushed to death by a falling piano, but the jaunty music and sight gags made it clear that we were meant to be laughing at the Supernatural version of Groundhog Day. It just wasn't easy for Jared Padelecki to play it that way, per EW:
Luckily, Jensen Ackles was hilarious as he found new ways to play Dean right before dying. Check out a montage of Dean's deaths, and try not to grin at the craziness:
Take away the jaunty music, however, and it's easy to see why Jared Padalecki had such a hard time filming "Mystery Spot." Padalecki played Sam's heartbreak and frustration every single time he had to watch his beloved big brother die, and it had to be exhausting. Throw in the fact that he and Jensen Ackles are off-screen BFFs, and his explanation that "Mystery Spot" was hard on him makes a lot of sense.
The episode got pretty dark after the end of the Groundhog Day gag as well, so Jared Padalecki didn't even get a break from the gloom and doom after he was done filming Dean's many deaths. Sam became a twisted version of himself after Dean's final death as he tried anything and everything to bring his brother back to life. The reveal that the Trickster/Gabriel had been manipulating the whole scenario to prepare Sam for Dean's upcoming real death and damnation definitely meant that the episode ended on a pretty depressing note. "Mystery Spot" is a classic episode of Supernatural that was as funny as it was dark, and we're lucky that Jared Padelecki was able to turn a solid a performance even when his job was harder than usual.