The 10 Most Gut-Wrenching Episodes of 'Dawson's Creek ' That Still Stick with Us, 20 Years Later

It's been 20 years since Dawson's Creek first premiered and almost 15 since it stopped providing us with tearjerker fodder, but true fans will never forget

Photo: Columbia/TriStar International Television

It's almost impossible to believe that it's been two decades since we first met Dawson, Joey, Pacey and Jen in the fictional, sleepy-yet-tumultuous town of Capeside, Massachusetts. But alas, it was Jan. 20, 1998, that Dawson's Creek splashed onto screens in its debut on The WB (which was eventually replaced by The CW).

From the first time Katie Holmes' Joey Potter scaled a ladder that led to the Steven Spielberg-adorned bedroom of the titular character, played by James Van Der Beek, tweens and teens within five miles of a television were instantly hooked. Next-door-neighbors-turned-BFFs forced to grapple with their maturing hormones using vocabulary years ahead of the norm? It was the perfect storm for kids during a time when the internet was just starting to pick up steam and the hardest parts of life were figuring out how to get Sun-In to actually work in their hair, how to time cassette players just right to record songs off the radio and how not to make their Discmans skip.

Tag-teaming with a '90s soundtrack featuring the likes of Jewel, Edwin McCain, Billie Myers and Sixpence None the Richer, the drama-filled plot lines of Dawson's Creek's six seasons defined an era in a way no series before or since it has. It had kids asking their parents awkward questions like, "Why would someone use leather straps and Crisco at the same time?", "Why can't I go spend the night in so-and-so's bed?" and "Why does Dawson walk his dog every morning?" (It was a euphemism for masturbation. Yes, really.)

With a main-event cast featuring the destined-for-greatness Michelle Williams as Jen Lindley and Joshua Jackson (a long way from his Mighty Ducks days) as Pacey — who sleeps with a teacher within the blink of an eye but eventually captures every heart with his roguish charm — plus supporting love from Kerr Smith, Meredith Monroe, Busy Philipps, Mary-Margaret Humes, Broadway vet Mary Beth Peil and more, Dawson's Creek delivered a bevy of lessons on first love, creating your own destiny, figuring out how to make the most out of life, friendship and everything in between.

The payment for this beautiful blip in sharp-scripted pop-culture history? A fated lifelong search to find our own soulmates and a huge heaping of tears — every single one worth it to experience this show following the chorus of Paula Cole's "I Don't Want to Wait" every week for five and a half glorious, angst-ridden years. (And thanks to Hulu, over and over again until the end of time.)

Here are our 10 most heartbreaking and emotional episodes of Dawson's Creek, 20 years later.

1. Season 1, Episode 1: "Pilot"

If there was an episode that could predict Williams as the breakout big-award winner for acting later in life, "Pilot" is the furthest one had to look. Initially entering the series as something almost out of a dream (so much so it is used again in a trance-like flashback during the series finale), Jen Lindley exits a taxi and introduces herself to the gang. Joey Potter, of course, is instantly intimidated, and thus would begin the infamous Jen vs. Joey Debate of 1998.

Even more breathtaking than Williams' entrance, though, was her scene beside the bed of Jen's dying grandfather, which was actually the scene she auditioned with that got her the part. The youngest cast member at the time, Williams kicked off the first of countless tearjerker moments peppered throughout the series just from her first solo performance.

And let's not forget Pacey Witter, who — like Riverdale's Archie Andrews after him — all but hooked up with English teacher Tamara Jacobs in this very first episode. Not gut-wrenching in the same way, but all the same.

Standout Quote: "Grams, I'm an atheist." — Jen Lindley

2. Season 1, Episode 12: "Beauty Contest"

While many fans remember the episode where Joey enters the Miss Windjammer pageant in the hopes of winning $5,000 toward her college tuition for her rendition of "Own My Own" from Les Misérables or Pacey's outlandish monologue in the style of William Wallace as the only male contestant,there was a lot more going on.

"Beauty Contest" is the first time Dawson Leery sees — truly sees — his lifelong best friend as something more. Jen instantly picks up on this backstage as they watch Joey perform, and Dawson grasps it even harder afterward when he and Joey have yet another conversation about how their feelings are changing. It's no surprise their first (real — the staged one in "Detention" doesn't count) kiss was only one episode away.

Standout Quote: "It's just makeup — and hairspray — and tomorrow I'll be back to being Joey. Just Joey. The too-tall girl that lives on the wrong side of the creek." — Joey Potter

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3. Season 2, Episodes 14 and 15: "To Be or Not to Be"/"…That Is the Question"

This two-parter revolved around Jack McPhee — who is new to Capeside, alongside his sister Andie — coming to terms with the fact that he is gay and being forced by the actual worst teacher in the history of teaching to read a poem out loud that he is not ready to read.

If the close-to-tears tone in Jack's voice and Mr. Peterson forcing him to continue reading weren't enough to get waterworks going, the moment Pacey spits in the latter's face was (secondary to the cheers, of course).

The second part sees an extremely emotional Jack pleading with his estranged father (played by the late David Dukes) to face the situation head-on, and the acting by Kerr Smith during this heated exchange still has many fans wondering why he doesn't have an Emmy on his home mantel.

Luckily, Jack has a huge amount of support from his sister, friends and Jen's Grams. And he and his dad do work it out — but not for a season and a half.

Standout Quote: "If Jack is gay, he doesn't need your judgment, young man. The Lord above will be the one to judge him, as he will judge all of us." — Evelyn "Grams" Ryan

4. Season 2, Episode 20: "Reunited"

The end of sophomore year is rough for Andie McPhee, who was just introduced at the beginning of the season and has slowly been descending into scary territory, hearing her dead brother Tim's voice and seeing visions of him. In "Reunited," she breaks completely, spiraling inside a locked bathroom.

She finally allows her boyfriend Pacey and brother Jack to comfort her — but what happens over the summer when she's away getting help made it difficult for all Pacey fans to ever rejoin Team Andie.

Standout Quote: "You have to, Andie. You have to choose. And I'm begging you, from the bottom of my heart, to please choose me. Open this door, come out here, and choose me." — Pacey Witter

5. Season 2, Episode 22: "Parental Discretion Advised"

Joey's complicated relationship with her father comes to a head in season 2's penultimate episode, which sees her going against her gut instincts by wearing a wire to send him back to jail for dealing drugs yet again — something that led to the family restaurant, the Ice House, burning down as a result of a deal gone bad. (Don't worry — Pacey eventually reopens it.)

Even sadder than the tears shed by the Potter family as its patriarch surrenders himself over to the police? The broken relationship between Joey and Dawson. The boy whom she has loved her entire life and has seemed to grow up with a perfect family (save the whole cheating thing and, a few seasons later, Mitch Leery's literal death by ice cream) suddenly becomes someone Joey doesn't recognize anymore.

Standout Quote: "Some situations are too tragic to have a hero." — Dawson Leery

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6. Season 3, Episode 20: "The Longest Day"

Season 3 remains one of if not the strongest season of Dawson's Creek in that it represented the true climax of the series. Boiled down to one episode, that climax is "The Longest Day," when Joey and Pacey finally work up the (admittedly hesitant) courage to tell Dawson they have romantic feelings for each other. It's told from three different points of view, which also makes it a pretty unique episode, emotional impact aside.

As one would expect, Dawson reacts very poorly, even though he was the one who asked Pacey to keep an eye out for Joey after Dawson himself rejected her. But that's textbook Dawson — and it doesn't change the fact that anyone who has been on the receiving end of betrayal not only from their best friend but also their assumed romantic soulmate knew what the poor guy was feeling, lash-outs and all. And it sucked.

Standout Quote: "Ever had one of those days you wish you could live all over again?" — Joey Potter (voice-over)

7. Season 3, Episode 23: "True Love"

Season 3's finale packed a lot of punch in different ways: Mitch and Gail Leery remarry, Joey sails off into the sunset with Pacey, Jack and his dad finally reach an understanding. But most importantly and notably, it was the birth of the Dawson Leery cry face meme.

It happens when Joey runs off after his parents' wedding. So not only did the poor guy have to watch his parents tie the knot for a second time, but he becomes the outcast third wheel yet again in the romantic life of his two best friends. Savage.

Jack and his dad have an extremely heartwarming scene in this episode, when Mr. McPhee finally accepts that his son is gay with literal open arms, and the two sweetly hug it out. On the kitchen floor.

"True Love" was also the first time on network television two men were shown kissing, which seems late now but at the time was pretty wonderful and, yes, long overdue.

Standout Quote: "I didn't ask to be gay." — Jack McPhee / "No more than I asked for a gay son … but boy, am I glad I got one." — Joseph McPhee

8. Season 4, Episode 20: "Promicide"

Pacey spends two entire seasons making everyone fall in love with him as Joey does (remember when he watched her sleep, and as a teenager that wasn't at all creepy but now sort of is?), then promptly smashes that visage with a temper tantrum at the gang's prom that ends with him dumping Joey in front of the entire senior class.

And it's not because Joey is upset that he messed up the flowers and the limo or other items on the laundry list of things he thinks he has to do to make Joey happy. It's because deep down, Pacey thinks he isn't good enough for her, and she's going off to college to become something great while he's stuck in Capeside with his insecurities.

For those who had been rooting for this couple from the beginning, it was a rough 44 minutes. Luckily, the writers put Joey and Pacey together in the end, and for that they deserve the world.

Standout Quote: "You break my heart into a thousand pieces, and you say it's because I deserve better?" — Joey Potter

9. Season 5, Episode 15: "Downtown Crossing"

While seasons 5 and 6, aka the college years, didn't quite embody the charm of the first four seasons, a few episodes stand out in memory. One is "Downtown Crossing," which tells the story of a time Joey gets mugged but grows close to her assailant after he is hit by a car following the scuffle.

At the hospital, she slowly learns that not only is he a dad, but that his daughter is named Sammy — which further encourages Joey to draw parallels between his situation and her difficult one with her own father.

Standout Quote: "It's funny how things are always shifting like that. One day, you have the upper hand, you're in control, and the next, you're totally at somebody's mercy." — Joey's mugger

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10. Season 6, Episodes 23 and 24: "All Good Things … "/"Must Come to an End"

Dashing all hopes of Williams making a non-ghost return to any future Dawson's Creek revival that the '90s teen soap gods decide to one day bestow upon thirty-somethings, Jen bites the bullet in the series finale. "All Good Things … "/"Must Come to an End" takes place five years in the future when the gang is 25 years old — which, for Creek fans in 2003, seemed so old, and now … does not. Especially for death.

Player 1 in the "We haven't drowned viewers in their own tears yet, so let's give it one last shot" game? Jen's video message to her baby daughter Amy, whom she puts BFF Jack in charge of raising alongside his boyfriend: Pacey's brother Doug, who turns out to be gay after all after six seasons of tasteless jokes from Pacey about it.

The video (shot by Dawson, natch) rivals Williams' first appearance in the series. The audience sees the same strong person she was 10 years previous, radiating through her words and her eyes as she speaks to her daughter's future, and Dawson, somehow, manages not to shed even a single tear.

And who can forget the moment she finally succumbs to her illness, with Grams by her side — a woman who has cared for Jen as if she were her own child over the past decade who can only utter "I'll see you soon, child" as her final words to her granddaughter. Tissues, anyone?

Standout Quote: "The thing that I've come to realize, sweetheart, is that it just doesn't matter if God exists or not. The important thing is for you to believe in something, because I promise you that belief will keep you warm at night, and I want you to feel safe always." — Jen Lindley

Honorable Mention: Season 3, Episode 22: The Anti-Prom

Fans know the moment — the line that sealed the deal between Pacey and Joey shortly before they boarded the True Love during the summer of 2000 and set off Dawson's iconic cry face.

Pacey notices Joey is wearing her late mom's bracelet, and recounts word for word and detail for detail the exchange between them when she told him the day she found it, six months earlier.

Joey: "You remember that?"


May every Dawson's Creek fan have found their Pacey and still be living happily ever after.

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