Five years after its finale, The Vampire Diaries is possibly more popular now than it was during its original run, especially with audiences who love worldbuilding. Amid ionate break-ups, equally ionate make-ups, complicated love triangles heightened by teenage emotion, and as much gore as the CW could get away with, there were flashback episodes that gave fans further insight into the supernatural world.
Stretching from Classical Antiquity to 1994, the series slowly built a magical alternate timeline of Western Civilization, twisting history to fit into its mythology. With it, each era brings its charms and wonders that allow The Vampire Diaries universe to feel truly fleshed out.
The Nineties
Trapped together in what turned out to be Kai's prison world, Damon and Bonnie were forced to repeat the same day in May 1994 over and over again. The Season Six storyline both pumped some much-needed life into the series and firmly established Bonnie and Damon's unconventional yet profound friendship.
There's a lot of fun nostalgia in these episodes: flannels, grocery store carousel rides, ironic orange juice cap messages, hand-held video cameras, and most importantly, an excellent soundtrack.
The Seventies
Damon, Elena, and Rebekah's trek to New York City to hunt down Katherine brings them to a nightclub where, in flashbacks, Damon proves himself a villain during his toxic affair with his brother's best friend.
The design team clearly had a blast recreating the New York punk scene of the late 70s based on the attention to detail in these scenes. The black, graffiti walls, general dirtiness, and ripped clothing are authentic to the period. Sadly, Lexi's hairstyle looks a little too much like Jennifer Aniston's to as "punk rock", but everything else is pretty spot on.
The Sixties
Season Five gave viewers a couple of brief flashback scenes on Election Night 1960, one of the only times an actual historical event was depicted on the show, if only as a backdrop. Damon unwittingly killed Enzo's former love while the distracted townspeople celebrated J.F.K's win over Nixon.
Stefan's collegiate white shirt, black tie, and black peacoat with its popped collar made him look like a young Beatle - the stylists even tried to make his hair resemble a mop-top.
The Fifties
Damon channels Danny Zuko in a classic white tee and black leather jacket combination in a Season Five flashback that portrayed his kidnapping and abuse at the hands of a secret society.
"The Cell" further explained Damon's backstory and was one of the only times vampires were portrayed as victims. The Augustine Society serves as a metaphor for the dark hypocrisy hidden beneath a veneer of gentility. It's a pointed criticism of the 1950s, a decade dominated by McCarthyism.
World War Two
In "We'll Always Have Bourbon Street," a lonely and depressed Damon wishes to his brother in the war overseas, yet bows to Lexi's demand to stay away from when she claims Stefan will relapse under his influence.
Though the episode's portrayal of how the U.S. military works were far-fetched at best, the point of the flashbacks was to further explore Damon and Stefan's volatile history. The jazz, slicked-back hair, uniforms, pin curls, and berets were just a fun bonus.
Roaring Twenties
Season Three's "The End of the Affair" revealed a period of Stefan's life removed from his memory by Klaus. His depravities are stacked up against the Originals' - and it's hard to say whose were worse.
The series loved combining sex and violence at nightclubs and this episode was no exception. The music, beaded flapper dresses, and champagne towers all make the show's depiction of Chicago in the Roaring Twenties one of the most enjoyable flashbacks in The Vampire Diaries.
Edwardian Era
In her brief time on the show, Sage taught Damon important life lessons, proved pivotal to several plot lines, and served as a foil to Rebekah. Her poignant scene with Finn in Season Three about the beauty of immortality proves they were both gone too soon in The Vampire Diaries.
While female boxers did exist in the 1910s, Sage's costuming in a very short romper and bare legs is an example of the show's frequent use of artistic liberty in its flashback scenes.
American Civil War
Modern culture loves to romanticize Confederate vampires and TVD was no exception; brothers Damon and Stefan were turned by the wily Katherine during the waning days of the Civil War.
The most bizarre part of the show's version of Central Virginia in 1864 is how (besides a few shots of Damon in uniform) there doesn't seem to be a war going on at all. There are barely any references to the hundreds of battles fought in the area, or the lack of food, goods, and horses by that point in the war.
The Renaissance
The flashbacks that are shown in "Katerina" and "Klaus" proved to be some of the most essential to world-building. Katherine's beginnings in Bulgaria helped humanize one of the most enigmatic villains on the show.
The content is great, but the costuming (especially in regards to headgear) and general historical accuracy do not make a whole lot of sense. While The CW doesn't have the highest budget, the network would also go on to produce a historical series with Reign so a little more effort could have been made. Nevertheless, the show's reveal of Klaus in Tudor England before showing his real face in the modern-day narrative was clever and unorthodox.
Medieval Italy
The elusive Cure to vampirism was introduced in Season Four when a flashback episode showed the Originals' first encounter with the Five in Medieval Italy. This ultimate McGuffin would remain vital to the series until the final few minutes.
Episodes exploring the Mikaelsons' past always excited fans. Eventually, the characters began to overshadow the main cast and outgrew their time in Mystic Falls, leading to the The Originals.
Viking Age
The Vampire Diaries' version of the Viking Age proposed a small band of Norse warriors wandered much further south than Newfoundland and established a settlement in present-day Virginia. The alternate timeline served to connect the Originals to the Mystic Falls Gang.
The human Mikaelson siblings are depicted as sensitive and refined - soft, even; while this was meant to highlight their changes after turning, it is an objectively absurd portrayal of Vikings.
Classical Antiquity
Qetsiyah created the Cure in Biblical times, while Sybil's roots can be traced back a millennium and a half earlier. While neither of these depictions is even remotely historically accurate, at least the characters wore togas.
Yet the series was never concerned with replicating history; it was creating a mythology for the TVD universe that explained the origin of supernatural beings. However, taking the extra steps to ground the storylines in real history made the mythology more believable - and engaging.