Alternate Realities Sam
Alternate universes became a primary theme of the later seasons of the Supernatural story, but altered realities, dream worlds and supernaturally created fantasies invaded Sam's life long before then. Glimpses of these "what could have been" Sams gave Jared the opportunity to play around with Sam's personality, gifting us with wonderfully memorable character portrayals.
Djinn Dream!Sam - 2.20 "What Is and What Should Never Be"
After being captured by a djinn, Dean imagined a perfect life where he and Sam never lost their mom, never learned about monsters and the supernatural, and never took up hunting. This dream version of Sam got the normal life he and Dean always thought Sam deserved. His unblemished innocence is conveyed in Sam's face as he interacts with a brother he hardly knows. 
Sadly, Dean's utopian life meant that he and Dream!Sam never became close. 
Without hunting, the bond that defined Dean's reality was never formed with his brother.
Dream!Sam went to law school, became engaged to Jessica and lived across the country from Dean in California. 
Sheltered from hunting, this Sam didn't save hundreds of people with his brother, and had little patience for Dean's drinking and laissez-faire attitude. 
Despite his sheltered life, Dream!Sam's hard core family values were hiding deep inside him, at least in Dean's mind. When Dean asked for Sam's help, he put aside his doubts and showed up at his brother's side - despite being unprepared, unskilled and highly skeptical.
Jared again played two different personalities for Sam in this story. While the majority of time was spent with the dreamt version of Sam, the real Sam was desperately trying to save Dean from the djinn. 
The contrast in emotional intensity was striking...
and a big part of the story's impact.
Sam Wesson - 4.17 "It's A Terrible Life"
Two years after Dean's dream world, he and Sam were forced into a another altered reality by the angel Zachariah.
In this life, Sam worked in tech support at Sandover Bridge & Iron, Inc. 
He and Dean didn't know each other but were once again drawn together when Sam became suspicious of "dreams" of fighting evil with Dean. 
After supernatural forces invade their boring, predictable, civilian lives, Sam's naturally analytical mind figured out that they were dealing with a ghost, and Smith (Dean) and Wesson united to battle the evil...
proving that the brothers' bond, and their drive to be hunters, were stronger than even an angel's power to wipe their memories and supplant their lives with a less fateful existence. In this episode, there weren't any scenes of the real Sam, so Sam was his altered self throughout the entire story.
Ted Talk!Sam - 14.13 "Lebanon"
An alternate time line gave us the gem of TedTalk!Sam!
Much like the real Sam, this Sam was well-educated and a deep thinker.
Unlike Sam, though, TedTalk!Sam was confident and comfortable speaking in the public arena. He was obviously a respected leader in his field...
but was definitely not someone Dean would want riding shotgun in Baby on cross country road trips! 
Nope! You can hear Dean jamming on the brakes at the first sign of that smirk looking over at him from the passenger seat! There may have been some inside humor in Sam's recorded speech, though. Note Jared looking straight into the camera.
If you're a diehard Jared fan, you know that he memorizes his scripts while running on a treadmill. Might he have been lampooning himself with his Ted Talk treadmill desk recommendation? Too funny! But while Jared might have seen a little of himself in TedTalk!Sam, it's clear that our Sam didn't approve!
Neither did Dean!
For once, the brothers agreed on something! Sam decided the Ted Talk version of him had to go!
Hunter Corp. (aka "Trust Fund") Sam - 15.13 "Destiny's Child"
Was this a dream or a nightmare? Much like the Sam who delivered Ted Talks, Trust Fund Sam was also rich, famous and a bit more... delicate than our Sam.
As a co-owner of Hunter Corp, the very successful business enterprise started by John, this alternate universe Sam grew up in luxury. He managed the "family business" of fighting monsters from an ivory tower, proud that he never had to get his hand dirty in the field. He and Dean were still partners, providing entertaining banter with their sibling rivalries... 
... but the brothers' refined sensibilities were easily annoyed...
or scandalized by the slightest faux pas of etiquette or suggestion of hard work. Their disgust generated priceless facial expression that said just as much about their personalities as their clothes, their conversation and their actions!
There's no arguing that Sam's taste in hair styles was a win in either universe, though! 
Throughout this journey with our beloved Sam, we've looked back at 18 different personalities he endured in the 15 years we spent with him. Seen through over 300 images of Sam's facial expressions, Jared flawlessly portrayed Sam as evil, addicted, broken, brave, rich, poor, young, old, bewitched, bewildered and beguiled! Besides these many character tangents explored in this 6-part monograph, we've also been beside Sam as he's been hurt, grieving, enraged, obsessed and downright dangerously scary. Which "Sam" did you like the most? Did I miss your favorite Sam? Is there an aspect of Sam you'd like featured in its own photo essay? Share your thoughts about Sam below in the comments!
Enjoy the full Con-tinual panel, "Who Wore Sam Winchester Best?" with panelists Michelle Crowley, Carole Stokes, myself and host Gail Z. Martin.
Continue the fun with more of Nightsky's Supernatural insights!
If Sam is your jam, enjoy our deep character studies, "Breathtaking" photo essays and fun articles dedicated to Sam Winchester!
If Dean is your man, enjoy "The Many Faces of Dean Winchester"!
Use WFB's Supernatural Episode Guide to look back at any of the episodes mentioned above.
Grieving Sam vs BAMF Sam is a study of his best and his worst days as himself.
