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He’s been called everything from problematic to groundbreaking, stereotypical to revolutionary — and is as much a staple of the rom-com as meet-cutes and dirtbag fiancés. Meet the Gay Best Friend, a figure who’s evolved dramatically over the past three decades. Here we identify the key players who changed the trope for the better.

Buddy (Charles Grodin) in 1984’s The Woman in Red

This is perhaps the first notable GBF in the modern rom-com canon. Gene Wilder’s 1984 film — about a married man who becomes obsessed with meeting a model — wasn’t exactly a box office sensation, but it quietly moved the needle with its normalizing depiction of Buddy, a gay man who was simply “one of the guys.”

Hollywood (Meshach Taylor) in 1987’s Mannequin

On the exact opposite end of the spectrum, there’s Hollywood Montrose, window-dresser for Prince & Company department store. He’s a compelling, larger-than-life presence, an early example of a femme-gay cliché brought to sparkling life by Taylor, who died in 2014. “Quite honestly, things were very stereotyped back then,” Mannequin casting director Marci Liroff admits. “But Meshach was just funny. He had it in his bones. His timing was great, and there was something wonderfully endearing about him.”

Sammy (Steve Zahn) in 1994’s Reality Bites

So we reach an early, notable example of the ’90s gay sidekick, armed with quips and with a penchant for dispensing empathetic advice. Sammy plays right-hand man to Lelaina (Winona Ryder) in Ben Stiller’s Gen X comedy, and crucially, he gets a small but potent storyline of his own: finally coming out to his parents.

Gareth (Simon Callow) in 1994’s Four Weddings and a Funeral

Like Woman in Red’s Buddy from a decade earlier, Gareth plays GBF to the male lead, a less common occurrence. But this was a fuller portrait, a major step forward in the onscreen depiction of queer couples. Gareth is a spirited man in love with the relatively shy Matthew (John Hannah). Rather than being otherized, their romance treated with nuance and empathy to the film’s end, when Matthew tenderly eulogizes his late lover during the film’s titular funeral.

George (Rupert Everett) in 1997’s My Best Friend’s Wedding

1997: the year the GBF went prestige. Along with Greg Kinnear’s Oscar-nominated turn as gay artist Simon Bishop in As Good As It Gets, Rupert Everett drew raves for his turn as MBFW’s George Downes, the quintessential one-gay-man support system. He pretends to be Julianne’s (Julia Roberts) fiancé. He acts as her conscience. But in the most groundbreaking moment, he’s at the center of the film’s conclusion — dancing with Julianne in the final frame. Typically, the GBF cheers from the sidelines; here, he plays the hero.

George (Paul Rudd) in 1998’s The Object of My Affection

At last, the gay best friend plays the romantic lead… kind of! Rudd’s George agrees to raise his single best friend Nina’s (Jennifer Aniston) baby, but things get complicated when, despite knowing George is gay, she falls for him. His character represents the ideal version of the trope—charming, handsome, witty — but more depth comes with a main role. And he gets a love story — yes, with a man — of his own.

Damian (Daniel Franzese) in 2004’s Mean Girls

Teen movies tend to work off stereotypes, often resulting in broadly drawn queer characters. But Tina Fey flipped the script with Mean Girls’ Damian. “Damien was the first [main] teen-movie gay character I can think of who wasn’t shoved into a locker or had his head pushed into a flushing toilet or whatever. It was an opportunity for him to just be one of the cast and have an arc and have a story,” says Franzese, who came out as gay in 2014. “I really wish I had someone like Damien [growing up], who could’ve made my high school life a little smoother, a little easier.”

Brandon (Dan Byrd) in 2010’s Easy A

Rather than being victimized and bullied over his sexuality, Brandon in Easy A goes on a humane, painful journey toward self-acceptance after he concocts a lie with best friend Olive (Emma Stone) to convince his school he’s a “straight stud” (to disastrous results). “I didn’t even think about the fact that he was gay too much, even though I know that was his entire plight in the movie,” Byrd reveals. “I was just trying to humanize him.”

Oliver (Nico Santos) in 2018’s Crazy Rich Asians

The GBF timeline overall is inescapably white. What Crazy Rich Asians’ Oliver proves is that this trend limits not only the kinds of queer faces put on screen, but queer experiences as well. Having grown up in Singapore, Oliver is forced to navigate a very conservative (and rich) world and assert his gay identity in subtle but empowering ways. He’s also flamboyant — which Santos says shouldn’t be seen as regressive. “I hate that femininity in a gay men is a ‘stereotype,’” says Santos, who is openly gay. “Femme people exist, and they are layered and they are complex and they are intelligent.” Indeed, he adds: “You don’t encounter characters like this ever.”

Every day until Valentine’s Day, Entertainment Weekly is celebrating our special romantic-comedy-themed Untold Stories issue. Check out all of our behind-the-scenes tidbits, reunions, and oral histories — and follow #LoveEWstyle on Twitter and Instagram.

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