15 Lesbian Kisses From Hollywood We'll Never Forget

August 2024 · 12 minute read

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Over the past couple of years, a trend has developed of soft-core lesbian films being seamlessly integrated into mainstream television shows in order to further storylines and eliminate the risk of ambiguity caused by simply alluding to a romantic relationship between two partners of the same sex (I’m looking at you, Bert and Ernie).

Netflix originals such as Orange is the New Black and Sense 8 have featured vivid girl-on-girl action; sometimes to enhance the plot of the episode, sometimes just for the sake of having it in there, but always to the delight of the viewers. The streaming service also has a comedy-drama series based on the all-female GLOW wrestling promotion of the 1980s in the pipeline and you had better believe there’s gonna be a lot of lesbian action in that.

Of course, same sex make-out sessions have been featured in Hollywood movies and gossip rags for decades now, they’ve just never been quite as easy to access. Whether it’s for a split second in the middle of a film from the 90s or under a street lamp on an LA sidewalk, the kisses are there for anybody willing to search for them. In order to save you those countless hours of research, today we’re looking at 15 of Hollywood’s hottest lesbian kisses both in and out of the movies. And we’re doing it all in the name of journalism, I swear.

Let’s get started.

Sandra Bullock & Scarlett Johansson

In early 2010, Miss Congeniality star Sandra Bullock dropped off the face of the earth after it was revealed that her husband, motorcycle fanatic Jesse James, had been seeing multiple women behind her back. After weeks of silence and avoiding the press, Bullock returned to the spotlight at the 2010 MTV Movie Awards to receive the MTV Generation Award and clear up rumors regarding her demise, among other things.

Presumably, in an attempt to show the world that she had moved on and to give the media something to talk about beyond her marital woes, the newly single star awkwardly embraced presenter Scarlett Johansson before throwing caution to the wind and planting a passionate, though not nearly long enough, kiss on the Match Point star.

Carmen Electra & Paris Hilton

Having made her name in the television series Baywatch, as well as in underwhelming parody movies such as Date Movie, Meet the Spartans, and Disaster Movie, former Playboy model Carmen Electra isn’t exactly the most reserved person in the world. Neither is Paris Hilton, who achieved her greatest fame by spending her father’s money and drinking too much.

For this reason, it should be no surprise that Electra and Hilton caused a bit of a stir (and that’s to be it mildly) when they appeared on stage together at the 2004 MTV Movie Awards.

Upon receiving the MTV Movie Award for Best Kiss for her three-way Starsky and Hutch make out session, Electra turned to Hilton, who had presented her with the popcorn themed trophy, and invited the heiress to join her in another titillating kiss as an ecstatic audience (and Snoop Dogg) looked on.

Katy Perry & Miley Cyrus

As a teenager, Santa Barbara native Katy Perry pursued a career as a gospel singer, which is more than a little ironic considering the fact her breakthrough song came in the form of the 2008 hit I Kissed a Girl. Miley Cyrus had a similarly innocent start, starring in the modern Disney Channel classic Hannah Montana before also abandoning her squeaky clean ways in favor of risqué performances and much-publicized sexual affairs with both men and women.

In early 2014, while performing as part of her Bangerz tour, Cyrus noticed Perry in the audience and beckoned her to the front row, where she then surprised the California Girls singer with a kiss, much to the delight of those in attendance. Unfortunately, the kiss only lasted a few seconds, with Perry revealing she pulled away after Cyrus tried to slip her that infamous tongue.

Angelina Jolie & Peta Wilson

Angelina Jolie has made no secret of her unique sexual desires in the past. Over the years, she has discussed her love of bondage and S&M in great detail, citing her belief that such activities are essential to the strengthening of a relationship. Jolie became so closely associated with the BDSM community that there was even talk of her directing the original film adaption of 50 Shades of Grey, a job that instead went to Sam Taylor-Johnson.

Jolie has also freely discussed her bisexuality and has not shied away from partaking in same-sex exchanges with her fellow actresses. One such exchange took place at the 1997 Cable ACE Awards when the future (and future ex) Mrs. Pitt was seen locking lips with La Femme Nikita star Peta Wilson.

Miley Cyrus & Stella Maxwell

While Katy Perry’s infatuation with the same sex seems to be mostly a marketing ploy, Miley Cyrus appears to appreciate the female form every bit as much as she claims. Shortly after ending her engagement to Hunger Games star Liam Hemsworth, Cyrus entered into a committed relationship with Stella Maxwell, a Belgium-born Victoria’s Secret Angel. The evolution of the relationship between Cyrus and Maxwell from friends to lovers was captured on camera both by the pair themselves and the ever-present paparazzi.

In the summer of 2015, a video was shared online of the two passionately making out under the cloak of darkness. The romance between the two women eventually burned itself out and Cyrus rekindled her relationship with Hemsworth, thus ending her foray into girl-on-girl activities.

Denise Richards & Neve Campbell

Actress Denise Richards spent four years married to former Two and a Half Men star and noted addict of various substances and activities Charlie Sheen. When you’re married to Charlie Sheen for any length of time, you had better be pretty open-minded. Thankfully, Richards was.

Prior to marrying Charlie Sheen, Denise Richards displayed her willingness to try anything in the 1998 erotic thriller Wild Things. The film quickly gained notoriety for its various vivid sex scenes and girl-on-girl action. Perhaps the most enduring image of the movie shows a soaking wet Denise Richards passionately making out with an equally hot Neve Campbell in a swimming pool after a brief but apparently arousing argument. Although the film was rated R, it is a safe bet that the majority of those who paid to see the critical failure were teenage boys.

Madonna & Britney Spears

Long before the likes of Katy Perry and Miley Cyrus were setting the charts on fire with racy lyrics about their scandalous sexual exploits, there was Madonna. In 1995, Madonna very nearly sent her critics to the madhouse when she released “Human Nature”, an almost five-minute anthem about the perks of sexual promiscuity. The video for “Human Nature” caused nearly as much outrage as its lyrics and featured Madonna, clad in a skintight latex catsuit, being touched and caressed by backing dancers of both sexes.

Almost a decade later, Madonna’s friskiness landed her in the headlines again when she shared a kiss with her early 21st-century counterpart, Britney Spears. The two locked lips on stage at the 2003 MTV Video Music Awards, to the shocked applause of the celebrity-laden audience.

Drew Barrymore & Liv Tyler

During the late 90s and 00s, Drew Barrymore’s sexuality was a major topic of conversation among the press and would-be Hollywood pundits. Speaking about her personal life in 2004, the former child star likened being with another woman to exploring your own body, before adding: “When I was younger, I used to go with lots of women. Totally. I love it.”

In 1999, at the tail end of her aforementioned younger years, Drew Barrymore shared a kiss with Liv Tyler – daughter of Aerosmith frontman Steven Tyler – on the red carpet of that year’s Academy Awards. In the years that have passed since that kiss, Barrymore has embarked on multiple heterosexual relationships and has even had two children, but Hollywood has not forgotten her much-publicized years as a sexually flexible eccentric.

Michelle Rodriguez & Cara Delevingne

Over the years, Avatar star Michelle Rodriguez has dated the likes of Vin Diesel and Zac Efron. However, the actress and screenwriter has made no secret of her bisexuality, declaring in 2013 that she falls “under the B category of LGBT”.

In 2014, Rodriguez began a relationship with Cara Delevingne, an openly bi-sexual model who movie fans will recognize as Enchantress from the 2016 blockbuster Suicide Squad. Rodriguez and Delevingne have since parted ways and the latter moved on to a relationship with St. Vincent (the singer, not the Roman Catholic saint).

Although Michelle Rodriguez and Cara Delevingne are no longer an item, their brief romance spawned several memorable pictures, including a series of photos of them making out in the ocean during a holiday in Cancún, Mexico.

Madonna & Christina Aguilera

When Madonna made out with Britney Spears, she fulfilled the wish of teenage boys – and, indeed, adult males – the world over. Literally seconds later, she did it again when she kissed Genie in a Bottle singer Christina Aguilera.

Performing a titillating mashup of her classic hits “Like a Virgin” and “Hollywood”, the self-proclaimed material girl was sandwiched between Spears and Aguilera, who were both at the height of their success. Madonna is famous for her charitable efforts and willingness to give back, so I guess it should come as no surprise she felt the need to share a kiss with Aguilera after granting one to Britney. 13 years later, Aguilera would kiss another girl on international television when she locked lips with a contestant on the show The Voice, on which she was supposed to be an impartial judge.

Selma Blair & Sarah Michelle Gellar

Sarah Michelle Gellar achieved her greatest fame playing the titular character of the 90s supernatural drama Buffy the Vampire Slayer. However, most males who grew up in the 1990s will more fondly remember her from the 1999 teen drama classic Cruel Intentions.

In the film, Selma Blair’s character, Cecile Caldwell confides to her friend Kathryn (played by Gellar) that she has “Never even gotten to first base with a guy”. Gellar, decked out in a pair of sunglasses and wide-brimmed hat, offers to teach Cecile how to make out in a hands-on lesson. The two proceed to kiss not once, but twice (the second time with tongues), in a scene that could rival Sharon Stone’s Basic Instinct legs uncrossing for the title of Most Rewound Scene in Cinema History.

Stella Maxwell & Kristen Stewart

You may remember Stella Maxwell as the Victoria’s Secret Angel who had the privilege of being the lesbian lover of Miley Cyrus during the controversial singer’s time away from Hunger Games star Liam Hemsworth.

After her relationship with Cyrus came to an end, Maxwell entered into a relationship with Kristen Stewart, star of the Twilight film series. The relationship came as a surprise to many of Stewart’s fans, who had managed to remain unaware of her bisexuality despite her multiple relationships with other women in the past (not to mention her frequent declarations of being “so gay”). All doubts about the legitimacy of Stewart's relationship with Maxwell were removed earlier this year when the pair were caught sharing a kiss in the backseat of an SUV while holidaying together in Milan.

Sandra Bullock & Meryl Streep

The fiasco with Scarlett Johansson at the MTV Movie Awards was not the only time Sandra Bullock locked lips with another woman in 2010. Bullock shared a similarly wet kiss with Mamma Mia star Meryl Streep at the 2010 Critics Choice Awards.

Bullock later stated that the kiss was a good-natured attempt to embarrass Streep after months of back and forth ribbing between the two actresses, which began when she beat out Streep to win the 2010 Academy Award for Best Actress for her role in John Lee Hancock's The Blind Side.

Of course, the kiss didn’t mark Streep’s first foray into same-sex interactions in Hollywood. One of Streep’s earliest on-screen roles came in 1979 when she played the lesbian ex-wife of Woody Allen’s character in the award-winning black and white throwback Manhattan.

Ellen Page & Samantha Thomas

While giving a speech at the Human Rights Campaign’s 2014 Time to Thrive conference in Las Vegas, Juno star Ellen Page broke her silence on her sexuality and came out as gay, garnering support from both the public and the media, who quickly dubbed her an LGBT icon. In September of the following year, Page confirmed that she had entered into a relationship with Samantha Thomas who is an artist and surfer.

Although Page and Thomas have had no problem being photographed in public together, regularly appearing side by side at red carpet events, they have avoided public displays of affection. However, the two were snapped in the middle of a passionate welcome-home kiss back in April of 2016, when Thomas collected her actress girlfriend from LAX Airport.

Jenny Shimizu & Michelle Harper

Unlike many of the other celebrities on this list, Angelina Jolie’s historical same-sex escapades were not limited to brief kisses at awards shows or on red carpets. The openly bisexual actress is said to have had numerous sexual flings with women before embarking on her much-publicized relationship with Brad Pitt.

Of all those flings, the most well-documented was her one with model Jenny Shimizu. However, because the affair took place behind the back of Jolie’s then-husband Jonny Lee Miller, few intimate pictures exist of Jolie and Shimizu together. Thankfully, we do have this picture of the stunning Shimizu - who also claims to have been Madonna’s secret lesbian “booty call” - sharing a wedding day kiss with socialite Michelle Harper, whom she married just days after Jolie tied the knot with Brad Pitt.

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