In Supernatural's earlier seasons, Sam and Dean's paranormal hunting trips were sometimes interrupted by devious magical pranks. The high jinks began in Season 2's "Tall Tales," in which the brothers investigate a series of murders that smack of irony -- a serial animal abuser mauled by alligators -- and improbability -- a mean frat house kid killed by an extraterrestrial abduction.
Bobby, their resident lore expert come stand-in father figure, reckons the culprit is a Trickster, a reality-warping demigod that needs little further explanation. Except that, this Trickster really did need a lot more explanation. As is the hallmark of the archetype, there's an awful lot more to Supernatural's mystical swindler than meets the eye. And, over the course of several seasons, the character wound up becoming one of the show's most endearingly fascinating figures.
Back in Season 2, what could have been just another satisfying detour from the show's overarching plot ends on a lingeringly intriguing note. Satisfied that the suggested stake through the heart seemed to have done the trick, Sam and Dean depart the scene, leaving only us, the audience, to witness the Trickster's slain body disappear while the real one manifests nearby, ready to trick another day.
He was far from done with the boys, however, and each of his subsequent cameos in their lives became more elaborately twisted. Season 3's "Mystery Spot," a series highlight to this day, trapped the Winchesters in a Groundhog Day scenario with none of the charm or romantic payoff of the Bill Murray/Andie MacDowell classic. Instead, Sam is forced to watch his older brother die over and over again in ways that range from the everyday -- a car accident -- to the Looney Tunes-esque -- a falling piano. Each death results in time being reset to the beginning of the day.
Recognizing his hallmarks, Sam eventually catches the Trickster and demands he break the cycle. While the antagonist agrees, Sam's threat to off him in revenge forces the Trickster to get serious: killing Dean off for good and leaving a mourning Sam to live for months alone -- the cruelest joke of all.
When the Trickster pops up again to put the hunter out of his misery, he reveals the method to his madness was to break the brothers' troubling co-dependence. Sam didn't heed his lesson, but we sure learned something significant: there was a beating heart behind the demigod's devilish smile.
If the reality-bending fun of "Mystery Spot" wasn't enough, Season 5's "Changing Channels" really put the Winchesters through the metaphysical wringer. Shortly after they figure out that a quick-tempered man in Ohio probably wasn't beaten to death by the real Incredible Hulk, Sam and Dean are whisked into the fictional worlds of various television shows, from Dr. Sexy MD to a high-risk game show to a medical commercial that forces a frustrated Sam to proudly tell the viewers at home that he has genital herpes.
By this point, the brothers are working under the assumption that the Trickster's substantial power level identifies him as Loki, one of the world's best-known mischief-makers. However, Castiel, who tries to rescue the boys, is convinced the supposed Norse god is even more powerful than he's letting on.
With the use of an angel trap, Sam and Dean finally lay all doubt to rest. "Loki" is exposed as the Archangel Gabriel, which the Winchesters deduced by watching him easily fend off Castiel's advances and by the emotionally charged way he talked about his brothers, Lucifer and Michael, whose constant bickering led to the youngest Archangel running away from home and making a new one on Earth.
This is the first point of connection made between the Winchester family's dysfunction and God's, a humanizing quality for the higher beings that, as we later learn, also defines Lucifer's tumultuous relationship with the Father of Creation. Unlike Castiel's stilted mannerisms -- typical of most Angels fresh to the world of humans -- Gabriel, taking on Loki's face and character as "witness protection," has been living among his father's favored children for hundreds of years. And, as evidenced by his pop-culture literacy and fondness for human vices, he's been more than just surviving.
Of course, with the coming Apocalypse set to interrupt Gabriel's favorite vacation spot and his true identity laid bare, the Archangel drops the fun and games to make his intentions clear: he wants Dean to serve his purpose as Michael's vessel so that his family in-fighting can finally come to an end. It's a desperate sentimentality that lays the ache behind the jester's smirking bare.
Sentimentality is what eventually leads Gabriel to go back on his word, as well as a lifetime of indulgent self-satisfaction, in a surprising face-off against a freshly released Lucifer later in "Hammer of the Gods." Playing the hero suits his character arc thus far but does nothing for his survival rate. An emotional spat with his older brother saves Sam and Dean's lives but leaves Gabriel fatally wounded.
This is far from the end of his story, though. In a surprising twist -- though perhaps one we should have seen coming given Sam and Dean's multiple trips between life and death -- Gabriel is revealed to have pulled off a miraculous escape eight years ago thanks to the illusions that Lucifer dismissed as "hocus pocus." Gabriel seeks out the real Loki once more to help him regain his deep cover, only to be betrayed for, in Loki's eyes, allowing Lucifer to kill Odin.
In Season 13, we find him locked in a cell in Hell, gagged and broken after years of torture at the hands of Asmodeus, a Prince of Hell who Loki sold Gabriel to. Asmodeus used the Archangel's grace to juice himself up. Upon being rescued, Gabriel's road to recovery under Castiel, Sam and Dean's watch restored his powers but left him a changed being.
Much like the Old Testament incarnation of his father, the former Trickster goes on a smiting rampage, scorching the demon who held him captive and slicing his way through Loki and his crew of lesser gods, aided by the reluctant Winchesters. Revenge eventually gives way to gratitude and absolution as the youngest Archangel -- unsettled business firmly settled -- lets go of his Trickster moniker for good.
Ultimately, Gabriel's underlying tragedy and his penchant for heroics led him once again to his demise -- permanently, this time. He's persuaded by Castiel to return to his family home to prevent Heaven from falling to ruin, but first, in the wake of his perennially absent dad's second leave of absence, he has to put his affairs in order: travelling to Apocalypse World to fend off an evil, alternate universe version of his brother, Michael, keep their other brother, Lucifer, on a tight leash, and bond with his new Nephilim nephew.
No sooner did Gabriel seem poised to stop running and take charge of his cosmically chaotic family, he dies by the blade of an Archangel once again -- Michael, this time. In doing so, he also once again secures Sam and Dean's safety.
Understanding and appreciating humanity's flaws molded Gabriel into the most unpredictable and charismatic of Supernatural's higher beings. Between Michael's righteousness and Lucifer's rebellion, he was the first to offer a grounded perspective on the celestial drama that drives the entire show. After all, only a brother could get away with telling another brother that, even though they love them, they're also a "giant bag of dicks." Even if that brother happens to literally be the Devil.