The Vampire Diaries is not against throwing a flashback into the mix every once in a while — but not all glimpses into the supernatural past are created equal. In honor of the upcoming 100th episode (Season 5, Episode 11: “500 Years of Solitude”) — which will feature some flashbacks of its very own — here is a list of our 10 favorite flashback episodes.

10: Season 1, Episode 6 (“Lost Girls”)

It’s hard not to feel partial towards this flashback-heavy ep, which was not only the first to utilize the device, but the one that told the story of how Damon (Ian Somerhalder) and Stefan (Paul Wesley) met Katherine (Nina Dobrev) back in 1864. The costumes! The hair! The Katherine Pierce! TVD (and the Salvatores) would never be the same again…

9: Season 4, Episode 8 (“We’ll Always Have Bourbon Street”)

The Salvatore brothers in World War II uniforms? Count us in! This may not have been the most epic of flashback episodes, but it was fun to see Damon, Stefan, and Lexi (‎Arielle Kebbel) kicking it in 1940s New Orleans. And the scene in which we see Lexi convincing Damon not to go to war with his brother because he is a bad influence is truly heartbreaking — especially considering Stefan always assumed his brother totally ditched him. Sob.

8: Season 1, Episode 13: “Children of the Damned”

Our second glimpse into Mystic Falls, circa 1864, it showed just how crazy things got back in the day. Basically, the whole town turned on its vampire population resulting in some heartbreaking revelations. Also, Damon owned this episode. We see just how much he loved Katherine, and how hard he fought to try to save her.

7: Season 4, Episode 17 (“Because the Night”)

Are we the only ones who adore this episode that shows has Damon sporting his best punk rock look in 1970s NYC? The best flashback episodes are the ones that change the way we look at present-day characters and events and this one put some seriously troubling and interesting tones on Damon’s murder of Lexi in Season 1 (which was already a mega-troubling event). In the flashback, we learn that Lexi spent months in NYC trying to convince Damon to turn his emotions back on — and she kind of falls for him along the way. Damon tricks her into believing that his emotions are back on and that the attraction is mutual, only to leave her locked on a sunlight roof after a night of passion. Harsh.

6: Season 3, Episode 3 (“The End of the Affair”)

Klaus (Joseph Morgan), Rebekah (Claire Holt), and Stefan partying it up in 1920s Chicago? What’s not to like about that scenario? This flashback episode was stylish, romantic, and introduced is us to the character of Rebekah Mikaelson — the gift that keeps on giving. Not to mention the Klaus/Stefan bromance. We’re still kind of sad this dynamic wasn’t further explored on TVD. Oh, well. They’ll always have Prohibition!

5: Season 5, Episode 9 (“The Cell”)

Perhaps we’ll feel differently about this episode further down the road, but this recent Season 5 episode that showed us Damon’s five-year incarceration as an Augustine vampire in the 1950s felt seriously refreshing after the Silas/Amara/Tessa drama. It also gave us a big piece of Damon’s recent history: the answer to why he turned off his humanity (it was the feels over leaving Enzo to burn). Who knows if this storyline will reach a satisfying conclusion, but we’ll always have a soft spot in our heart for the story of Enzo and Damon’s prison-friendship.

4: Season 2, Episode 9 (“Katerina”)

Perhaps this is just anticipation for the additional Katherine backstory we’ll be getting in the 100th ep, but we adore this episode that gives us the deets on Katherine’s pre-vampire life. In a nutshell: it sucked. Back in 15th century, she has a baby who is ripped from her arms as soon as she’s born. This episode added another much-needed layer to this complex character, not to mention gave Nina Dobrev a chance to wow us with both her awesome acting chops and her Bulgarian language skills.

3: Season 3, Episode 22 (“The Departed”)

Though there may have not been old-timey hair and costumes in this flashback to Elena’s life right before her parents died, it shed some serious light on how much our heroine’s life has changed in a few short years. It also gave the big reveal that Elena had actually met Damon before she met Stefan, on the night of her parents’ deaths. It doesn’t hurt that this episode ended with Elena’s death and transition into vampirism, launching a whole new chapter in the TVD saga.

2: Season 3, Episode 8 (“Ordinary People”)

This is the one, guys! The episode that finally lays out the origin story of the Mikaelson family, aka the Original vampires. The episode that would grow to launch its own compelling spin-off series. In it, we learn how Klaus, Elijah (Daniel Gillies), and Rebekah were turned into vampires by their parents after their younger brother was killed by werewolves — we also learn the source of most of Klaus’ dangerous complexes: his relationship with his father. So good.

1: Season 1, Episode 20 (“Blood Brothers”)

Man, we love this ep that showed us Damon and Stefan’s transition to vampirism. It was surprising and heartbreaking to learn that Damon didn’t want to be a vamp, but Stefan convinced him. This show is at its strongest when it’s playing the nuances of this fraternal relationship — and this was one of the most important moments of their lives. (And deaths.)

Which flashback episode is your favorite? Your least favorite? Where do you expect the 100th episode to rank on the list? Sound off in the comments below!

The Vampire Diaries returns Thursday, January 23 at 8 p.m. on The CW.

Kayti Burt is a contributing writer for Wetpaint Entertainment with a penchant for all things pop culture. Follow her on Twitter and Google+!