20 Songs That Shaped My Lesbian Awakening (And Just Turned 20)

As a kid in 1998, living in a household where everything on TV over a PG-13 rating was locked behind parental control, there wasn’t much that captured my imagination beyond Xena: Warrior Princess and I Love Lucy reruns. Sure, as a latchkey-lite kid there was time to figure out the passwords every once in a while, but all that deciphering taught me two valuable lessons: that it was a waste of time, and that I had no business watching Oz at the tender age of 13 anyway.

Music was fair game though, and so my teen years were spent watching MTV (it used to be a channel for music back then) and VH1. Pop music helped shape me, and got me through some painful and awkward years as a young queer kid in a Catholic household coming to terms with my lifelong conflicted feelings for Kirstie Alley in It Takes Two. Music videos made me realize it wasn’t just Kirstie Alley I had these feelings for, but all women.

Making a playlist recently, I noticed most of my favorite throwbacks are from that time, and it made me realize 1998 had some serious bops. Here are 20 of them that shaped my lesbian awakening.

“The Boy Is Mine” – Brandy & Monica

https://www.youtube.com/watch?v=jBmkCoiHC2c

It might be hard to understand how a song about two girls fighting over one guy could inspire any kind of Sapphic feeling, but the music video explains some things. Brandy and Monica spend most of the time sulking in their respective apartments over a guy that’s clearly playing them both, but the match that sparked my fire was the moment in the end where Mekhi Phifer knocks on Brandy’s door thinking he’s slick, only to find Monica is also there before they slam the door in his face. Art is up for anyone’s interpretation and I interpreted this as two former rivals who have fallen in love and now live together and would soon be adopting two cats.

“This Kiss” – Faith Hill

Long before Taylor Swift glided across the line between country and pop with the finesse of a ballerina and the business savvy of a stockbroker, there was Faith Hill, whose country-lite pop hit “This Kiss” cemented her crossover status. It’s a song about a snog that you can sing along to without thinking about pronouns. It also features lyrics that my little gay ears immediately zoned in on where Cinderella tells Snow White she’s wanted a white knight with a soft touch and a fast horse before adding, “Ride me off into the sunset, baby I’m forever yours.”

I ship it.

“You Look So Fine” – Garbage

The first time I listened to Version 2.0, the album from which this single hails, I felt like someone was slowly pulling my heart out of my chest, and the first time I saw Shirley Manson in the video for “You Look So Fine” I wanted her to be the one to do it. Everything about her made my heart race; her red hair, her unapologetic feminism, the gritty melancholy in her voice. Sure, Garbage has always been an LGBT ally, but we all want Shirley Manson to sing us back to consciousness on a sandy beach and that’s the true takeaway.

“Ex-Factor” – Lauryn Hill

Lauryn Hill’s The Miseducation of Lauryn Hill is arguably one of the best albums recorded in the past 30 years. Hill’s meticulous blend of heart-wrenching lyrics and haunting melodies made her solo debut album an essential part of anyone’s music collection. It was not only an awards magnet, but a masterclass in what makes a great album. I was nowhere near experienced enough to understand the complexities of of “Ex-Factor” in 1998, but it did preemptively give me a go-to breakup song that I’ve revisited more than once since then, and no one gets it like Ms. Lauryn Hill.

“…Baby One More Time” – Britney Spears

I envy those who didn’t live through the stress of Britney vs. Christina. The pressure of picking between two pop queens was a demand I was not equipped to undertake then, nor am I now, but Britney came first so, let us all appreciate the schoolgirl outfit that both divided a nation of creepy adults who considered a 17 year-old girl’s midriff a perverse abomination, and united a generation of kids, queer and straight, who agreed that Britney Spears was a gift to pop music.

“Heartbreak Hotel” – Whitney Houston

It’s Whitney Houston, featuring Faith Evans and Kelly Price. I don’t think this needs much of an explanation. There are three beautiful women, Whitney’s got a white fur coat on, they sound amazing, there are no men in it. It’s the perfect video for a pretty good song.

“Reflection” – Christina Aguilera

Christina Aguilera’s debut single was from Disney’s Mulan, and it is a song written from the point of view of a girl who has to hide her real self from the world, pretending she’s something she isn’t for the sake of those around her. If you don’t see how “Reflection” is a coming out power ballad, then you’re probably straight.

“Are You That Somebody?” – Aaliyah

Aaliyah was a talented, charismatic, beautiful artist who overcame an ordeal no girl should have to overcome, and publicly no less. Despite the gossip that surrounded the release of her first album regarding her relationship with R. Kelly, she achieved admirable success during her short career in both film and music, and out of the perseverance came “Are You That Somebody?” Apart from being an absolute bop, I dare you to watch this video and not be existentially changed by Aaliyah in that crop top and baggy pants.

“Jumper” – Third Eye Blind

Coming out is a process, and that process begins with first coming out to yourself. For many it can be a struggle. Whether the challenge is spiritual, familial, or something else, coming to terms with one’s identity can be bleak, and “Jumper,” which is a song Stephan Jenkins wrote about a gay high school friend who committed suicide, takes all the toxic, self-harming thoughts and turns them into an anthem about survival and leaning on each other. That kind of message really resonates when you’re at catechism class and a nun is telling you being gay is a sin.

“Suavemente” – Elvis Crespo

“Suavemente” has been playing at every Latinx function since its release in 1998. From baptisms to weddings, this song is still the best way to fill up a dancefloor. And since the only acceptable public girl-on-girl contact in Latinx family parties is dancing, it’s also the best way to dance with the really cute daughter of the family friend who only comes around for special occasions.

“I Don’t Want To Wait” – Paula Cole

Technically, this song was first released in 1996, but it blew up in 1998 when it was used as the theme song for Dawson’s Creek, and it will forever be a song I associate with my love for Joey Potter, the character played by Katie Holmes in the teen drama, and my theory that she was in fact a lesbian who deserved to live her best life with Jen Lindley, played by Michelle Williams.

“Too Much & Stop” – Spice Girls

The cinematic masterpiece that was Spice World premiered in 1998, and from it came the boppiest soundtrack we could have hoped for. Spice Girls gave young girls a sisterhood philosophy and four Sex And The City type characters to identify with. I was a Ginger who secretly wanted to kiss Mel B.

“I Get Lonely” – Janet Jackson

https://www.youtube.com/watch?v=D8MeGKjTLp4

Janet Jackson had me at “Rhythm Nation” when I was four, but “I Get Lonely” made me nervous and squirmy in a way I didn’t yet understand. I’m pretty sure this the root of my thing for women in ties.

“Kind and Generous” – Natalie Merchant

Natalie Merchant has a voice like a beautiful witchy lesbian that lives in a cabin by a river, where she grows her own food, has a pet goat, and occasionally takes in queer runaways from nearby villages. I’m convinced that if Joni Mitchell and Stevie Nicks had a baby, you’d get Natalie Merchant, human embodiment of Lilith Fair and mother to Florence Welch, probably.

“Ray of Light” – Madonna

There’s no particularly Sapphic reason to include this song except that Madonna and Rosie O’Donnell’s relationship is my favorite celebrity friendship of the 90’s and when Madonna was on Rosie’s talk show to promote Ray of Light, it was the League of Their Own reunion we deserved.

“Torn” – Natalie Imbruglia

Where were you when you found out “Torn” is a cover? I don’t personally recall but I do remember learning Natalie Imbruglia was dating David Schwimmer and recognizing immediately that she was far too good for him or any man.

“Malibu” – Hole

Everyone was in it for Courtney Love, but my heart belonged to Melissa Auf der Maur, the band’s ethereal bassist. Not long after the release of this single, Auf der Maur left Hole to pursue a solo career, but she will always be the reason I changed the channel every time my mom walked in the room and the video for “Malibu” was on, just in case my gay was showing.

“Uninvited” – Alanis Morissette

Something truly terrible must happening in the world for gay icon Alanis Morissette to have become culturally irrelevant. She didn’t have to go this hard for a movie soundtrack, and yet here she is, and wigs are flying off all over the place.

“Believe” – Cher

Cher said “Gay rights!” when she gifted us the epic Believe album, which still holds up today. The iconic diva has been blowing people’s expectations out of the water throughout her career, but no one saw the explosion of “Believe” coming. The single was everywhere, including Spanish radio stations, and it introduced a new generation to Cher’s iconic body of work through TV specials like Behind The Music on VH1, a made-for-TV biopic titled The Beat Goes On: The Sonny and Cher Story, and even reruns of Cher’s variety show from the 70’s, simply titled Cher. I know the gays like to claim Cher, but citing Silkwood as reference, I believe the lesbians have a strong case for custody.