Generally speaking, Sam Winchester is below the likes of Dean, Crowley, Bobby, and even Castiel when it comes to the funniest characters on Supernatural, but that does not mean he does not provide some of the show's most laugh out loud moments. Over fifteen seasons, while he tends to be on the more serious side, Sam delivers a lot of great funny quotes.
Sam is usually at his funniest during abnormal situations such as being stuck in a time loop, being soulless, or cursed. These situations provide audiences with some of the best comedic quotes in the series.
Cutting The Tension
"I Think You Totally Should Have Been Jamming Eye Of The Tiger Right There."
Sometimes the intense, emotional moments with Sam and Dean need to be cut with a little bit of humor. This is usually provided by Dean, but here it comes from Sam following a pretty powerful speech from Dean.
This is Sammy's response to Dean talking about going out swinging against Lilith and the demons. It is made funnier not only by Dean's jamming out to 'Eye of the Tiger' in "Yellow Fever" but by Dean's response of "Oh, bite me. You know, I rehearsed that speech too."
Drunk Sam
"You're Bossy... And Short."
The boys drink a lot throughout Supernatural's fifteen seasons, probably an unhealthy amount, but rarely are they shown to be massively drunk. When they are, though, it can lead to some hilarious moments such as this from Sam.
It is the unexpectedness that adds to the moment. Coming fairly early in the show, Sam is a straight arrow a lot of the time, not as irresponsible as Dean, which is probably where this insult comes from. It is a funny reversal on the fact that it is usually Sam's tallness getting joked about in the show, rather than Dean's height in relation to him.
Soulless Sam Has No Empathy
"Third Kind Already? You Better Run Man, I Think The Fourth Kind Is A Butt Thing."
Season 6 is never ranked as the best season of Supernatural and was pretty disappointing coming off of the Kripke-era, which was consistently excellent. Nevertheless, it had some great stuff, including soulless Sam, who was hilarious on numerous occasions.
This comes in one of Supernatural's wildest episodes ever, "Clap Your Hands If You Believe," and it is spoken to Dean over the phone, who is freaking out about a close encounter. It is one of many brilliant comedic moments and quotes in the episode that may not be for everyone but is incredibly entertaining.
Justified Anger About A Lack Of Salt
"What Kind Of House Doesn't Have Salt, Low-Sodium Freaks!"
A lot of the funnier Sam moments that come in his regular day-to-day life are not jokes or quips like Dean, but rather ive-aggressiveness or frustration that is inadvertently funny, such as this dig about a household having no salt.
It is such a quickly delivered line and one that just oozes annoyance from Sam, who has a point; it is odd for a house not to have salt easily accessible. He gets flustered and frustrated a bunch in Supernatural, but this is an unexpectedly funny moment during these outbursts.
Sam Threatens God
"No, Not Really. We Have Guns, And We'll Find You."
Back in the Kripke-era, before he was Supernatural's most powerful and arguably evilest villain God, Chuck was a prophet and the writer of the Supernatural novels, a meta storyline that infuriated Sam and Dean.
After witnessing a Supernatural convention - and, of course, hunting during it - Sam says Chuck can continue to publish books before quickly revealing he was lying and threatening God himself with guns. It was funny at the time but is even more so in hindsight, given everything fans know about Chuck and how their story together unfolds.
Playing His Part
"I've Got Genital Herpes, But Now I Take Twice-Daily Herpexia To Reduce My Chances Of ing It On."
One of Supernatural's best and funniest episodes of the Kripke-era is "Changing Channels," which requires Sam and Dean to play their roles at the behest of the Trickster, whether that be in a procedural cop show, Dr. Sexy, or a herpes medication commercial.
The combination of Dean's glee at Sam's despair and Sam's hesitant delivery as he looks right into the camera makes this a highlight comedic moment in the episode. The Trickster, more than all the other villains outside of Crowley, really knew how to entertain and put the boys in funny situations.
Oscar-Worthy Performance
"If There's A Key, There Has To Be A Lock."
"The French Mistake" is one in a handful of brilliantly executed meta episodes in Supernatural's run and sees Sam and Dean have to act as Jared Padalecki and Jensen Ackles on the set of Supernatural.
The premise just begs for hilarious moments, and it is clear the performers involved are having an absolute ball. This quote comes when Sam and Dean are forced to put their method on and act in front of the cameras. It takes talent to act as a bad actor, and both Jared and Jensen do so terrifically.
Groundhog Day
"Right, You're A Mind Reader. Cut It Out, Sam. Sam! You Think You're Being Funny, But You're Being Really, Really Childish. Sam Winchester Wears Make-Up. Sam Winchester Cries His Way Through Sex. Sam Winchester Keeps A Ruler By The Bed And Every Morning When He Wakes Up…"
"Mystery Spot" is another entry in the catalog of hysterical Supernatural episodes. It is one of Sam's best episodes in the show, with most of the humor in the episode coming through his anguish at being stuck in a time loop where he has to watch Dean die over and over and over again.
This quote comes when Sam is verging on losing his mind, and both he and Dean speak it in unison. It is another well-executed comedic moment by both actors and is a standout moment in an episode that gives fans such gems as the continuous "Heat of the Moment" jamming from Dean and some absurd but uproarious deaths.
Soulless Sam Has No Attachments
"Oh, No, Like Half An Hour Ago."
One of the funniest things about soulless Sam is his stoicism and sheer lack of empathy that leads him to deliver great, sometimes even ridiculous, lines in such a deadpan manner.
This is in reply to UFO hunters who enquire about Dean's abduction and if it happened when Sam was a child, with them assuming that is the case thanks to Sam's also hilarious "I've had time to adjust." The moment is made all the funnier by his subsequent hooking up with the UFO hunter.
The Most Iconic Comedic Sam Line
"I Lost My Shoe."
Some quotes in Supernatural have and will continue to stick in fans' minds, being synonymous with the characters who speak them, such as "Hey, Assbutt!" or "Driver picks the music, shotgun shuts his cakehole." This quote is one of Sam's most iconic.
Like most of Sam's funniest quotes, this comes through bizarre circumstances, this time through a bad luck curse thanks to a rabbit foot, coming in one of Supernatural's funniest and most memorable episodes, "Bad Day At Black Rock." It is hilariously delivered, and the fact it stands out in an episode full of laughable Dean quotes is a testament to how funny audiences find it.
