Michelle Williams (Jen Lindley)
Before she became a Hollywood A-lister and three-time Oscar nominee—most recently for her dazzling portrayal of Marilyn Monroe in My Week With Marilyn—Michelle Williams starred as Jen Lindley, arguably the most tragic character on the teen TV drama Dawson’s Creek. Jen, a reformed wild child, was a New York transplant and obvious foil to the chaste Joey (Katie Holmes) whose hard-partying past always came back to haunt her. She moved to the Creek to live with her grandmother, and among her laundry list of accomplishments, she dated Capeside High’s star QB, Henry Parker (Michael Pitt), engaged in a no-strings-attached sex arrangement with Pacey (Joshua Jackson), and took Dawson’s virginity in college. During the series finale—spoiler alert!—Jen dies of a fatal heart condition, leaving behind her 1-year-old daughter and Grams.
Katie Holmes (Joey Potter)
Prior to becoming Mrs. Tom Cruise and her tumultuous relationship with actor Chris Klein, Katie Holmes was just a small-town girl from Ohio when she was cast as Joey Potter, the cutesy tomboy and BFF/neighbor of Dawson. Joey and Dawson eventually become a romantic couple at the end of Season 1, before realizing they’re better off as friends. Then, Joey dates Jack McPhee (Kerr Smith) before he realizes he’s gay and finally ends up falling for Pacey Witter (Joshua Jackson), after losing her virginity to him during the show’s third season. The couple breaks up when Joey goes off to Worthington College, but during the show’s season finale, it’s revealed that they’re back together again as a couple living in New York.
James Van Der Beek (Dawson Leery)
The protagonist of the series, Dawson is an über film geek—and aspiring filmmaker—who worships the oeuvre of Steven Spielberg. He’s longtime pals with the tomboyish girl next door, Joey (Holmes), and only realizes his love for her after he’s dumped by Jen (Williams). However, the couple breaks up at the end of Season 2, after Dawson convinces Joey to wear a wire and bust her father for selling drugs (yes, that happened). Dawson eventually enrolls in USC to study film, but drops out and moves to Boston to be with his friends. He eventually loses his virginity with Jen during New Hampshire’s Hookset Film Festival in Season 5, moves to California, and romances an actress. In the series finale, Dawson is the executive producer and chief writer of The Creek, a coming-of-age teen series based on his time growing up in Capeside.
Joshua Jackson (Pacey Witter)
Prior to wooing Troy actress Diane Kruger, actor Joshua Jackson was already a child star thanks to his leading role in The Mighty Ducks movies. In Dawson’s Creek, he played Pacey, Dawson’s hell-raising best friend. Pacey causes a minor scandal when word gets out that he lost his virginity to his 36-year-old teacher in Season 1, and eventually starts dating the emotionally unstable Andie McPhee. During Season 3, Joey loses her virginity to Pacey, and the two fall in love. After the two break up, Pacey lands in Boston, working at a classy restaurant called Civilization, and begins a physical relationship with Joey’s roommate, Audrey Liddell (Busy Philipps). After serving time working as a security guard in Capeside and even as a stockbroker in Boston for Audrey’s father’s firm, Pacey ultimately becomes the owner of the Icehouse, a restaurant in Capeside, and ends the series back with Joey.
Seth Rogen (Bob)
Before his scene-stealing turn in 2005’s The 40-Year-Old Virgin and star-making role in 2007’s Knocked Up, Seth Rogen made a cameo in one episode during the sixth and final season of Dawson’s Creek as Bob, a sarcastic stoner with whom Joey’s college roommate, Audrey, has a regrettable one-night stand. “We porked,” boasts Bob when Joey answers the door amid a smoky haze. It’s revealed toward the end of the episode that college girl Audrey is only using 21-year-old Bob as an excuse to buy her booze and make her parents incredibly upset.
Michael Pitt (Henry Parker)
He’d later star as a third of an incestuous ménage-à-trois in Bernardo Bertolucci’s 2003 film The Dreamers, as well as a vicious bootlegger in the HBO series Boardwalk Empire, but Michael Pitt first gained fame as Henry Parker, the freshman star QB of Capeside High, during the third season of Dawson’s Creek. He soon becomes completely infatuated with Jen, who is a junior, and they begin dating. However, Jen quickly embarks on a sexual relationship with Pacey, which causes drama between her and Henry. At the end of the season, Jen ends up choosing Henry, but Pitt exited the show because he reportedly felt the role wasn’t challenging enough, so they wrote him off during the fourth season premiere, saying he broke up with Jen and went off to private school on a football scholarship.
Jane Lynch (Mrs. Witter)
Years before she’d win a Golden Globe as Sue Sylvester, the bullying cheerleading coach on the Fox TV series Glee, Jane Lynch was a little-known comedienne whose claim to fame was serving as a member of Christopher Guest’s comedy troupe. She guest-starred in one episode, “The Te of Pacey,” during the fourth season of Dawson’s Creek as Pacey’s overbearing, hyper-religious mother, Mrs. Witter. In the episode, Joey visits Pacey’s family for Christmas dinner and witnesses firsthand how his parents belittle him.
Ali Larter (Kristy Livingstone)
Prior to her role on the hit NBC series Heroes and her epic throwdown with Beyoncé in the movie thriller Obsessed, the fetching blond actress Ali Larter played Kristy Livingstone, the head cheerleader of Capeside High, on a two-episode arc of Dawson’s Creek. Kristy is the object of Pacey’s desire, and he employs his geeky new female friend, Andy McPhee, to help him get her. Later on, after Pacey and Andy fall for each other and begin a romantic relationship, she is heartbroken to find out that Pacey still isn’t over Kristy when she catches him flirting with her. In a fun twist, Larter would later star as the ditzy, whipped-cream-bikini-sporting head cheerleader—alongside James Van Der Beek—one year later in the sports comedy Varsity Blues.
Chad Michael Murray (Charlie Todd)
Murray had already had a popular arc on the WB series Gilmore Girls prior to his stint as musician Charlie Todd during the fifth season of Dawson’s Creek, but was still a new face (he’d later go on to fame as the star of the Dawson’s Creek rip-off series One Tree Hill). Charlie dates Jen while the two attend Boston Bay College, until Jen finds out Charlie’s been cheating on her and, as payback, tricks him into getting naked and then locks him out of his dorm room. When Joey joins Charlie’s band, Aggressive Mediocrity, she has a brief fling with him that lasts only one episode before the two part ways.
Kevin Williamson (Series Creator)
After penning the hit teen-horror films Scream and I Know What You Did Last Summer, Kevin Williamson would go on to become the series creator, head writer, and executive producer of Dawson’s Creek from 1998 to 2003. In addition to writing the underrated horror film The Faculty, directing Dawson’s star Katie Holmes in the 1999 film Teaching Mrs. Tingle, and penning a couple of Scream sequels, Williamson would go on to create the 2007 CW series Hidden Palms, which was canceled after just eight episodes. He’d have more success, however, with the two supernatural TV shows he created after: The Vampire Diaries and The Secret Circle.