Teenage nightmare? From Britney to Olivia Rodrigo, the perils of being young, female and famous

Can Olivia Rodrigo and Billie Eilish escape the brutal treatment of young stars who came before?

“And I’m so sick of 17. Where’s my f***ing teenage dream?” Olivia Rodrigo asks on Brutal, the opening track of the 18-year-old’s debut album, Sour. But Billie Eilish reveals that 19 doesn’t get any easier on her second album, Happier than Ever.

Both singers are riding the latest teen wave in pop, with Rodrigo occupying more spots inside the top 10 at once than anyone else in history and Eilish topping album charts across the world, but it’s a wave that often comes crashing down.

In the family tree of teen pop stars, Rodrigo and Eilish sit just below the millennial generation of Disney stars such as Miley Cyrus, Demi Lovato and Justin Bieber, and two levels away from the elder millennials Britney Spears, Justin Timberlake and Christina Aguilera. Unlike most of their predecessors, their debut albums credit them as lead songwriters, giving them a stronger grip on their creative output from day one and allowing us to know them more intimately.

We've seen the pairing of fame and tragedy play out in every generation. Judy Garland, who was fed an amphetamine-based diet for The Wizard of Oz, would die of a barbiturate overdose in 1969

While both acts take Gen Z despondency into their hands, the difference between Rodrigo’s Sour and Eilish’s Happier than Ever is that Rodrigo firmly lives in the teen world while Eilish’s world has become warped by the pressures of fame. “Got a stalker walkin’ up and down the street, says he’s Satan and he’d like to meet. I bought a secret house when I was 17, haven’t had a party since I got the keys,” she sings over the twisted electronica of her latest single, NDA, wrapping the dangers of her celebrity around her trophies.


We’ve seen the pairing of fame and tragedy play out in every generation. Judy Garland, who was fed an amphetamine-based diet for The Wizard of Oz, would die of a barbiturate overdose in 1969; Karen Carpenter died due to complications from anorexia in 1982; Michael Jackson and his muddied legacy came to the fore in the 1990s; Drew Barrymore, who shot to fame in 1982 film ET aged seven, was addicted to drugs by the age of 12 and unemployable until the mid-1990s; and Spears ended up in a legal conservatorship, overseen by her father, Jamie, that has drawn criticism from lawyers and disability-rights advocates across the world.

Spears, who wore pigtails and a hiked-up school skirt in the video for her 1998 debut single, ...Baby One More Time, is the immortalised teenager. She was portrayed as the virginal girl next door before going on to have a public breakdown in her mid-20s. Controversy always accompanied her, whether it was intentional or exacerbated by pearl-clutching parents and sensationalist tabloids.

Over the past 18 months a new controversy has surrounded the singer as the fan-led Free Britney campaign, which has been running since early 2019 and claims that the conservatorship the 39-year-old has been under since 2008 is oppressive and unnecessary, has attracted heavy media focus. Associated conspiracy theories would have it that Spears was sending out cryptic SOS messages through her Instagram account. When this story moved from social media theories to the focus of the New York Times investigative film Framing Britney Spears, the media frenzy actually helped Spears, but her version of events is worse than the speculation.

In a rushed 24-minute external call to a Los Angeles courthouse in June, she said she had an intrauterine contraceptive device inserted to prevent her from having children and that she was put on lithium against her will, making it impossible to communicate with her parents. She said she was traumatised by the experience and described the conservatorship as abusive. Although nearing 40, Spears has been infantilised by people who work for her, including her own father, whose legal bills she also pays. She hurriedly ran through a list of daily freedoms she says she has been denied, saying she did not know when she would get the chance to speak so candidly again, and asked to have her life back.

There's a shocking self-awareness to Billie Eilish's lyrics, but her parents are aware of the dangerous tipping point that her career balances on

Her life has been legally restricted for the past 13 years but it’s a safe assumption that she hasn’t known independence for much longer than that. The lyrics to her 2000 single Lucky now feel prophetic. “And the world is spinning, and she keeps on winning but tell me what happens when it stops?” wrote Max Martin, Rami Yacoub and Alexander Kronlund – three Swedish songwriters who insert real-life issues of singers into their songs – for the then 19-year-old’s second album, Oops!... I Did It Again.

Like Eilish, Spears’s debut album ...Baby One More Time was teen focused but the side effects of fame found their way on to songs such as Stronger, 2001’s Overprotected and 2007’s Piece of Me. In the last of these, written as a retaliation to the media’s fascination with her life, which was then in a stage of upheaval due to mental illness and a custody battle over the then 26-year-old’s two children, she gets down to the crux of it: “I’m Miss American Dream, since I was 17. Don’t matter if I step on the scene, or sneak away to the Philippines, they’re still gon’ put pictures of my derriere in the magazines. You want a piece of me?”

There’s a shocking self-awareness to Eilish’s lyrics, but in The World’s a Little Blurry, her 2021 documentary film, directed by RJ Cutler, we see that her parents are aware of the dangerous tipping point that her career balances on. Maggie Baird and Patrick O’Connell, always in close proximity to their daughter, butt in when interviewers cross a line or remind her to behave when she becomes snotty over at a meet-and-greet with music executives.

Baird mentions Bieber, who acts as a confidant to superfan Eilish, and all of the times he’s “messed up”, referring to his arrests for driving under the influence, assault and reckless driving in 2014. She wonders out loud how anyone can be in the position of being a teen star without having parents around to mind them. Inadvertently, Baird becomes the narrator in the documentary; as an outsider, she has seen other celebrities lose control, but now, as an insider, she wouldn’t know how to stop it.

For many celebrities, control is the thing that marks their transition from child stars into adults but when your empire is built on teen appeal, it’s not an easy handover. Singer and actor Demi Lovato started their career on Barney and Friends in 2002 but when they became a staple part of the Disney scene in the late 2000s, their struggles with drugs and body image became public. In the 2021 documentary Dancing with the Devil, the 28-year-old is honest about the addictions, eating disorders and relapses that have plagued their career.

Released three years after Lovato nearly died from an overdose of oxycodone laced with fentanyl, this is the third film that follows their sobriety. In 2012’s Stay Strong, 20-year-old Lovato admits to smuggling drugs on to airplanes, and in 2017’s Simply Complicated, they reveal that they were on cocaine for most of the previous documentary. With such quick bouts between relapses and public declarations of being clean, Lovato’s films capture the true nature of addiction. Recovery takes time and relapses happen but when Lovato’s comebacks link in with a new album, it feels like an endless cycle that’s spurred on by fame.

In the late 2000s, celebrities' lives were broadcast in a way that had never happened before thanks to the arrival of Facebook, the increase in gossip websites and the widespread use of camera phones

I Hate Suzie, the 2020 British dark comedy created by Lucy Prebble and Billie Piper, encapsulates the lion’s den of A-list childhood fame and B-list celebrity adulthood. When Piper was 15, she became the youngest artist to debut at No 1 in the UK charts with 1998 single Because We Want To, so it’s quite fitting that she plays Suzie Pickles, a teen idol who shot to fame by winning an X Factor-style singing competition. Pickles is then faced with providing financially for her working-class family and being the innocent face of British music, but as a grown-up, details of her personal life spills into the tabloids and she’s painted and torn down as yet another unhinged famous woman.

Mirroring the reality of so many young famous women, Pickles’ emotional growth was stunted as a teenager and her dependency on drugs and sexual validation from a wider audience throws her into a state of grim existentialism and self-destruction. Piper, who can look back on her time as a teen pop prodigy as a different lifetime, brilliantly hits those marks in her writing and her performance.

In the late 2000s, celebrities’ lives were broadcast in a way that had never happened before thanks to the arrival of Facebook, the increase in gossip websites and the widespread use of camera phones. Between 2007 and 2011, it became fashionable to be seen as or seen with a car crash, with the under-21 cohort of film star Lindsay Lohan and reality TV icons Nicole Richie and Paris Hilton hamming it up for the cameras. All three were arrested for driving under the influence in 2007, with Lohan serving 84 minutes of a one-day sentence, Richie serving 82 minutes of a four-day sentence and Hilton serving five days out of 40. Their legal debacles overtook their on-screen work, causing more people to refresh the pages of Perez Hilton than tune in to their latest programme.

Today the power has moved from the hands of the paparazzi to the social media accounts of fans and trolls who demand a new level of perfection. In her song Overheated, Eilish talks about how her body has been objectified since she became famous and the unrealistic standards that have been set by other famous people on Instagram. In an interview with Spotify, she pinpoints the source of the outrage and twists the dagger in deep: “Why the f*** is it such a shock that I look like all of you?”

To be a relatable and normal teenager in the celebrity world is a fleeting freedom and, although she was home-schooled, Rodrigo’s music carries the pains and paranoia of being in high school. Having starred in High School Musical: The Musical: The Series – yup, that’s the actual name of the 2019 Disney+ mockumentary show – Rodrigo’s career has been sneered at by some as being totally manufactured when her debut single Driver’s License seemingly came out of nowhere in January and remains everywhere still.

Largely inspired by the autobiographical songwriting of Taylor Swift and the pop-punk finesse that Avril Lavigne pulled off in the early 2000s, she contains a cross-generational appeal that proves the timelessness and necessity of teen angst in pop music; for those going through it, it’s an outlet of expression and, for those way past it, it’s a rose-tinted yet thorny trip down memory lane.

Unfortunately, it reads like a rite of passage for famous teenagers to “go off the rails” but they work in an environment that’s practically designed to make people lose touch with reality. Where most teens have a wild phase that’s explored in underage discos, free gaffs or anywhere that a fake ID is accepted, celebrity teenagers have greater excesses to indulge in, more money to buy them with and a wider and less forgiving audience watching their every move. Just as Piper’s show portrays, the worst elements of fame are misogynistic and women will be held to a higher standard than their male peers, no matter what age they are.

With Eilish revealing the cruelty and repercussions of body shaming, objectifying, stalking and scrutiny faced by a teenager living in the public eye, and Spears gradually speaking her truth a little louder, by the time Rodrigo releases album number two, maybe the teenage dream will be less like a living nightmare.