With Pillion winning at the box office and shows like Heated Rivalry and Overcompensating gaining huge fanbases, it's easy to forget it hasn’t always been this way.
Actors clamoring to play gay roles is a fairly new phenomenon because it wasn’t that long ago that playing a gay character was a choice that could hurt your career.
But some Hollywood heartthrobs put those worries aside and took on roles that were often breaking new ground. Unfortunately, many of these huge A-list hunks played gay characters in roles no one remembers anymore.
Ryan Phillippe in 'One Life to Live' (1992-94)

ABC
Ryan Phillippe is best known for his ‘90s heartthrob status after starring in Cruel Intentions and I Know What You Did Last Summer, but he started his career playing a groundbreaking gay character on One Life to Live. Phillippe played gay teen Billy Douglas on the soap opera from 1992-1993, making him the first gay teenager to be portrayed on daytime television.
Joshua Jackson in 'Cruel Intentions' (1999)

Sony Pictures
With Sarah Michelle Gellar's kiss with Selma Blair taking up most people’s memories of Cruel Intentions it’s no wonder it’s often forgotten that Dawson’s Creek bad boy Joshua Jackson played gay high schooler Blaine Tuttle in the film. The character isn’t just subtextually gay; he's caught in bed giving a BJ to hot football jock Greg McConnell, played by Eric Mabius.
Robert Redford in 'Inside Daisy Clover' (1965)

Warner Bros.
Robert Redford, known for his hunky leading man roles, got his big break when he took on the part of closeted actor Wade Lewis opposite Natalie Wood in the cult classic Inside Daisy Clover. Rumor has it that Redford his character have interest in women, but it was also one of the first Hollywood movies in which a gay character is not ashamed of his sexuality and doesn’t die by suicide.
Antonio Banderas in 'Law of Desire' (1987)

Sony Pictures Classic
Iconoclastic gay filmmaker Pedro Almodóvar’s film Law of Desire stars Antonio Banderas early in his career, years before he made a name for himself in films like Philadelphia (where he also played a gay man), The Mask of Zorror, and Babygirl. The film follows Banderas, an intense young gay man from a conservative family, who becomes obsessed with a gay film director after watching one of his movies.
Robert Pattinson in 'Little Ashes' (2008)

Met Film Prod.
It’s understandable that most people don’t remember that Robert Pattinson played Salvador Dalí, in a movie about the Surrealist painter’s art school affair with Federico García Lorca (Javier Beltrán), since he was catapulted to superstardom that same year for playing a sparkly vampire in Twilight.
Leonardo DiCaprio in 'Total Eclipse' (1995)

Leonardo DiCaprio in 'Total Eclipse'
Warner Bros.
Shortly before Leonardo DiCaprio became one of the biggest celebrities in the world after starring in Romeo + Juliet and Titanic, he starred in the little-known film Total Eclipse. In the historical drama, DiCaprio plays French poet Arthur Rimbaud, who is in a steamy age-gap relationship with fellow poet Paul Verlaine (David Thewlis).
Javier Bardem in 'Second Skin' (2001)

Javier Bardem in 'Second Skin'
Lolafilms S.A.
In 2002’s Second Skin, Javier Bardem plays a gay orthopedic surgeon who has a secret love affair with a married man, whose wife discovers he cheated. The Spanish-language melodrama is an often-forgotten role in Bardem’s illustrious career, which has included his Oscar-winning role in No Country for Old Men and, more recently, Monsters: The Lyle and Erik Menendez Story.
Paul Rudd in 'The Object of My Affection' (1998)

Paul Rudd in The Object of My Affection
20th Century Fox
The future Ant-Man became a certified Hollywood heartthrob after starring in Clueless and Romeo + Juliet, before taking on a gay role in The Object of My Affection. In this ‘90s rom-com, Paul Rudd plays the gay best friend Jennifer Aniston’s character is in love with.
Will Smith in 'Six Degrees of Separation' (1993)

MGM
During his time on The Fresh Prince of Bel-Air, Will Smith starred as a young gay man in Six Degrees of Separation. Playing a gay man in the early ‘90s was not an easy choice, and Smith caved to social pressure and demanded to use a stand-in when his character was supposed to share a kiss with one played by Anthony Michael Hall, in a move Smith later called “very immature.”
Hugh Grant in 'Maurice' (1987)

Merchant Ivory Productions
Years before Hugh Grant’s breakout role in Four Weddings and a Funeral, he played a gay college student in the film Maurice. Set in Edwardian England, where homosexuality was illegal, Grant stars as Maurice Hall, who forms a romantic relationship with a wealthy Cambridge University classmate.
Daniel Radcliffe in 'Kill Your Darlings' (2013)

Sony Pictures Classic
Daniel Radcliffe’s role as Harry Potter has overshadowed much of his career since, but that’s a shame because it means few people remember that in 2013 he played a college-aged version of gay Beat poet Allen Ginsberg in the queer movie Kill Your Darlings.













