Confessions of a Teenage Drama Queen‘s Exuberance Is Still Delightful 20 Years Later

Standing in Target in 2004, I faced the most important decision of my young life: Should my first DVD purchase be Confessions of a Teenage Drama Queen or Ella Enchanted? I ended up choosing the former, and as it worked back then, this fateful selection meant that I played the iridescent disc over and over again until every line and beat of that movie worked its way into the grooves of my nine-year-old brain.

The film adaptation of Confessions of a Teenage Drama Queen (originally a novel by Dyan Sheldon) turns 20 today, and I hadn’t watched the movie in years until I went to revisit it for this piece. Confessions didn’t receive the critical acclaim of teen comedies like Mean Girls and hasn’t had the same lasting legacy as Princess Diaries or Bring It On, both of which have secured a comfortable place in the public’s memory of the noughties. I wasn’t sure I was even going to like the movie beyond my own nostalgia. (And reader, believe me, there is nostalgia galore: an orchestra of Mac laptops, cell phones mentioned as a flex, and idiosyncratic fashion that cannot be summed up in mere words.) However, upon revisiting it, I was surprised to find that Confessions is just as exuberantly delightful as I remembered. 

Confessions of a Teenage Drama Queen follows 15-year-old aspiring actress Mary Cep (Lindsay Lohan) as she moves from the hustle and bustle of New York City to Dellwood, New Jersey, which she dismissively dubs “Deadwood.” Insisting that people call her Lola (she tells a teacher that “everyone has referred to me as Lola since I was a squealing infant in my mother’s arms, I don’t even know who this Mary is”), she soon becomes friends with the shy Ella (Alison Pill) and enemies with entitled rich bitch Carla Santini (Megan Fox). That animosity is cemented when Lola beats out Carla for the lead role of Eliza in a reimagining of Pygmalion written and directed by their eccentric drama teacher (is there any other kind?) Ms. Baggoli (Carol Kane). When Lola and Ella’s favorite band Sidarthur breaks up, the two pull out all the stops to see the group’s last show. They end up spending the evening with the lead singer, Stu Wolff (“the greatest poet since Shakespeare” to Lola), but no one believes them thanks to Carla’s lies. The movie ends with Lola’s triumphant performance in the school musical and a surprise appearance from Stu that validates the two best friends’ story. 

Lola is a heightened predecessor to Lady Bird from Greta Gerwig’s 2017 film of the same name, packaged in a more frothy vehicle. Both are thespians dead set on becoming famous, and both adopt more “exciting” nicknames. They’re supported by their demure best friends (Lady Bird has Beanie Feldstein’s Julie, while Lola has Ella) and come from lower middle class families. Lola also resembles Anne from the novel Anne of Green Gables, with her imaginative and melodramatic manner. The way Lindsay Lohan utters “Ella Gerard, you are the sister of my soul,” immediately reminds me of Anne’s impassioned declaration that her neighbor Diane is her “bosom friend.” Sure, Lola bends the truth at times (more on that later), but her sincerity is genuine. Lohan is positively glowing here, and she makes a character that could be grating in the wrong hands extremely fun to watch.

Confessions of a Teenage Drama Queen may have the best portrayal of an adolescent girl’s inner life—not the serious, lonely moments, but the vibrant fantasies that fuel crushes and obsessions of the moment. We often cut from Lola’s humdrum life in New Jersey (which, for the record, still bursts with color and has that unmistakable movie sheen to it) to cartoonish scenes unfolding in her head, like the flashbacks of her parents’ whirlwind romance or the image of rockstar Stu Wolff holding onto a meteor as it hurtles towards earth. The props department deserve major kudos for their work on Lola’s scrapbook dedicated to Stu, which is covered with glitter and intricately decorated. Details like these give texture to the movie and give us a sense of just how much Lola is dedicated to Sidarthur’s frontman.  

Preteen and teenage feelings are simply so big. Confessions understands this and fully takes advantage of their cinematic possibilities, especially during Lola’s fantasy sequences. She may be chided as a drama queen during the film, but her intense emotions reflect the reality of teenage interiority. The smallest thing, like a snide comment from a classmate or a passing look from their crush, can send them into a tailspin—and that’s a thing of beauty. Adulthood requires us to moderate ourselves and exist within certain parameters in order to be taken seriously; Lola’s unabashed enthusiasm and, at times, ridiculousness are so contrary to our lives that it’s no wonder that Confessions of a Drama Queen was slated by movie critics (a profession historically dominated by men).

What makes this movie most endearing, though, is the friendship between Lola and Ella. Alison Pill, later known for The Newsroom and Scott Pilgrim vs. the World, is perfectly cast here as Ella, the shrinking violet and dorky rule follower. Born to wealthy, conservative parents and practically afraid of her own shadow, she’s in many ways Lola’s foil—so much so that Lola lies to Ella and claims her dad is dead because she knows Ella’s parents judge her mom (Glenne Headly) for being a single mother. (It bears mentioning that otherwise the movie doesn’t make a big deal about Lola’s parents being divorced—she seems very much okay with it, mostly lying to defend her mom’s honor and seem more “interesting.” The implication: Divorce is quotidian. Plus, her mom and dad are both portrayed as caring, amicable co-parents.) 

The two girls bond over their love of Sidarthur and their relationship forms the basis of the movie’s best emotional beats. From concerts to school plays, the story’s main action is fairly low stakes; the most gripping moments come from tension between the best friends. Lola picks Ella in a heartbeat when Carla dangles her friendship (and social status) as a potential reward if Lola ditches her nerdy new friend. The big fallout of the film isn’t when the two are barred from the Sidarthur concert they’re desperate to attend, but when Ella discovers that Lola has been lying about her father’s death. And later, when Lola’s confidence is at an all time low, Ella is the one who compels her to get out of bed and claim her rightful place on the stage. Thanks to Lola, Ella begins to break out of her shell and embrace a newfound confidence; meanwhile, Ella teaches Lola the importance of being truthful and considerate.

Confessions of a Teenage Drama Queen is also refreshing in its treatment of romance. Lola’s love interest, Sam (Eli Marienthal), is a mild-mannered classmate who loves working on his car and openly adores her. Notice that I did not include him in the movie’s summary—and that’s because he is incidental to the plot. There’s no tension about whether or not they’ll get together in the conventional sense: no jealousy, no misunderstandings, no hurt feelings. When she first meets Sam, Lola just questions whether she’d have time to date considering her busy schedule trying to reach stardom. The movie concludes with her deciding, “Maybe when my career is launched, I could have a boyfriend.” Sam is merely a benign afterthought, and that’s far from the norm for a noughties teen movie. Part of that probably has to do with the film mostly being aimed at preteens rather than fully-fledged teens; the idea of romance is more relevant than its reality. 

I want justice for Confessions of a Teenage Drama Queen, which was never claiming to be high art, but a romp meant to spark the imaginations of young kids. I could go into the old treatise about the long-time dismissal of media aimed at preteen and teenage girls, but we know that tune already. Let me just say that when I was nine, Confessions did a perfect job of getting me excited about growing older and the potential adventures of my teenage years. And as an adult, this movie reminded me of how much we sometimes need starry-eyed fantasy.

Clare Martin is a cemetery enthusiast and Paste’s assistant comedy editor. Go harass her on Twitter @theclaremartin.