Gay Best Friend: Tim in "Frankie & Johnny" (1991)

a series by Christopher James looking at the 'Gay Best Friend' trope   

Even before officially coming out, Nathan Lane (left) wasn't afraid to play gay in "Frankie and Johnny," pictured here with Kate Nelligan and Al Pacino.Especially in the early days, the inauthenticity of the “Gay Best Friend” trope came from straight actors mincing about to sell the part. The role is able to gain a whole lot of authenticity when a queer person is either writing or acting the part. In the case of Frankie and Johnny, both the writer and performer of the 'gay best friend' were gay, though both were not out. Theater legend (and out gay playwright) Terence McNally adapted his Off-Broadway play Frankie and Johnny in the Clair de Lune into a movie in 1991. He was able to get A-List talent to take the titular roles for film, with Michelle Pfeiffer and Al Pacino headlining. However, he also gave Nathan Lane one of his first breakout roles as Tim, the gay best friend and neighbor of Pfeiffer’s Frankie.

The 1991 film did not achieve the level of acclaim that McNally’s play did (thus it was the subject of a great This Had Oscar Buzz episode). Still, there are things to appreciate about this adaptation...

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Gay Best Friend: Damian in "Mean Girls" (2004)

a series by Christopher James looking at the 'Gay Best Friend' trope  

"She doesn't even go here" - Daniel Franzese steals yet another scene as Damian in "Mean Girls."Everyone remembers their first.

I don’t think Damian from Mean Girls was the first gay character I saw on screen. So many comedies throughout the 90s and early 00s used gay characters as easy punchlines or setup for gay panic jokes. However, Damian was the first time I saw someone who said it was ok to be gay. It would be many years before I myself came out, but Damian always felt like a touchstone to come back to. Damian is arguably the most famous example of the “Gay Best Friend” trope in 21st century movies thus far. He epitomizes the stereotype in both positive and negative ways. What stands out and makes him timeless is the way he takes up space within the school, especially at a time where gay kids often tried to “make it through” or “fade into the background.” If he was going to be a stereotype, by God he was going to let you know that he was the stereotype and you'd better pay attention...

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Gay Best Friend: Jane in "Boys on the Side" (1995)

a series by Christopher James looking at the 'Gay Best Friend' trope 

Incredibly disappointed I only now realized there was a road trip dramedy with Whoopi Goldberg, Mary-Louise Parker and Drew Barrymore.Long live the era of Whoopi Goldberg vehicles (aka the 90s).

Goldberg kick-started the 90s by winning a (well-deserved) Oscar for Ghost and headlining the smash-hit Sister Act. From there, we got a string of movies where Goldberg was the leading lady. Though they varied in quality and weren’t always progressive, it was impressive to see movie after movie built around a black actress. Who else could do Eddie, Bogus, The Associate AND Ghosts of Mississippi all in 1996? We’re going a year earlier for this week’s gay best friend. No, we’re not talking about Theodore Rex (though… should we). Instead, we are talking about the messy dramedy I didn’t know I needed in my life, Boys on the Side.

Unlike in past weeks, our gay best friend (technically) takes center stage. Jane (Goldberg) is a lesbian musician looking to get out of New York and move Los Angeles after a tumultuous breakup...

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Gay Best Friend: Oliver T'Sien in "Crazy Rich Asians" (2018)

 a series by Christopher James looking at the 'Gay Best Friend' trope 

Nico Santos does what every gay best friend does in a romantic comedy, stage a makeover montage.After a few retro episodes, we've made it back to modern examples of the Gay Best Friend trope. Crazy Rich Asians employs so many classic romantic comedy moments. When Nick Young (Henry Goulding) asks Rachel Chu (Constance Wu) to meet his family in Singapore, some nearby people overhear and set off a chain of texts that break the news to the entire Young family circle. Bright animated colors pop around the screen to demonstrate word spreading, recalling classic Doris Day title sequences of the 50s and 60s. This pastiche blends well with the grand opulence of the Young’s Singapore compound that feels in line with the worlds of Gentlemen Prefer Blondes and the recent Sex and the City movies. 

Any love letter to the romantic comedy has to employ one of the character mainstays of the genre: the gay best friend. This comes in the form of Oliver (Nico Santos), the rainbow sheep of the family...

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Gay Best Friend: Dolly Pelliker in "Silkwood" (1983)

 a series by Christopher James looking at the 'Gay Best Friend' trope 

This is a place for legends only.All roads lead to Cher.

Her second major drama role after Come Back to the Five and Dime, Jimmy Dean, Jimmy Dean the year prior, Cher won accolades and an Oscar nomination for Silkwood. As Dolly Pelliker, Cher brought humanity, warmth and vulnerability to Mike Nichols’ whistleblower drama. On the surface, she reads as the template for the lovesick, sad lesbian lusting after her best friend. However, in stretching herself for the role, Cher brings added dimension to what could’ve been a thin side character...

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