Gay Best Friend: Matt (Matthew Wilkas) in "Gayby" (2012)

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

How many of us have had babies with our straight female friend?Who doesn’t love gay lunacy? 

The classic straight girl-gay best friend trope takes center stage in the hilarious 2012 microbudget comedy Gayby. Unlike other films that have tackled this relationship (think The Object of My Affection), the film is set primarily in the gay world, rather than framed through the straight world. This movie has everything: gay comic book store drama, hookups lined up for every day in the week, early cameos from Girls stars Adam Driver and Alex Karpofsky plus, finally, an impromptu dance break.

Matt (Matthew Wilkas) and Jen (Jenn Harris) have been best friends since college. Both have been through their whole adult lives together and find themselves in the same post-relationship rut. Matt feels uncomfortable having one night stands with other men after his seven year relationship ended. Meanwhile, Jen feels her biological clock ticking and wants to have a baby. How to do it though? There’s no romantic interest to speak of in her life, and Matt has been the most consistent relationship in her life. She proposes they do it… the old fashioned way. Soon, Matt also becomes excited about the idea of having a child with Jen. He can move on to this stage of fatherhood and bypass the frightening world of being single.

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Gay Best Friend: Bernstein (Antonio Fargas) in "Next Stop Greenwich Village" (1976)

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

Look past the early "Chris" Walken appearance, Bernstein (Antonio Fargas - center) is the subject of this week's Gay Best Friend column.

Flying the nest can be simultaneously liberating and horrifying. On one hand, you have all this freedom to do what you want, when you want. Unfortunately, you have to learn how to take care of yourself and be self-sufficient. For those with tight knit families or over-involved parents, the horrifying can outweigh the liberating.

Next Stop, Greenwich Village laser focuses on the growing pains in this transition. The year is 1953. Larry Lapinski (Lenny Baker) leaves his parents’ home in Brooklyn to chase his dreams of stardom. His Mother, Fay (Shelley Winters), is utterly distraught and inconsolable. The umbilical cord is only hurt, not severed though. Larry's mother bursts in to his new life at the most inopportune times.  This column isn’t about Shelley Winters though, as much as it should be. Larry makes a variety of friends in Greenwich Village, one of which is Bernstein, played by Antonio Fargas, our gay best friend of the week...

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Gay Best Friend: Todd Cleary (Keir O'Donnell) in "Wedding Crashers" (2005)

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

Was Todd (Keir O'Donnell) the earliest inspiration for Gru from "Despicable Me?"I don’t love to complain (okay, sometimes I do). Most of the times I write this column to understand how gay representation in mainstream film has changed and evolved over the decades. Each shortcoming could be seen as another toe that LGBTQ+ characters stuck through the door of mainstream society. However, not all representations are good. Especially in the late 90s and early/mid 2000s, male focused comedies used gay characters as particularly malicious punchlines. As cartoonish as these characterizations are, they did paint a horrifying portrait of gay life to straight people. To gay people, these characters also served as a vision of what straight America hated about them.

My dark confession is that I love Adam Sandler comedies. They remind me of being an immature teenager and immediately bring back the sense memory of my hometown and a specific period in my life. Yet, these films were often the main source of these mockeries of gay life. (Though Sandler could be an equal opportunity offender, making himself the butt of the joke, too). Other mainstream comedies followed this formula to diminishing (and more demeaning) returns. The biggest R-rated comedy of this time was Wedding Crashers. The film grossed $205 million domestically (only to relinquish this title later to The Hangover 1 and 2) and was a word of mouth hit.

Today, the film’s success feels completely wild...

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Gay Best Friend: Buck (Mike White) in "Chuck & Buck" (2000)

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

Before his successful career took off, Mike White wrote and starred in the indie comic-thriller "Chuck & Buck."Mike White is an incredible talent. Currently on HBO, his miniseries The White Lotus has become a must-see weekly event. Between Enlightened, School of Rock, Beatriz at Dinner and impressive seasons on Survivor and The Amazing Race, White has been a great fixture of film and TV over the past couple decades. In honor of The White Lotus success, we thought we would travel back in time to one of his earliest performances and screenplays - Chuck and Buck.

The early digital film feels like a relic of another time, especially compared to White’s more polished HBO work as of late. The advent of digital allowed more filmmakers a chance to tell their stories as they were able to do it on the cheap. Much of Chuck and Buck looks like a painfully awkward home movie. Yet, that only heightens the discomfort one feels while watching this odd, comic thriller.

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Gay Best Friend: Christian (Justin Walker) in "Clueless" (1995)

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

You had me at "nice stems."Clueless is a perfect movie. The more time passes, the more the film is solidified as a bona fide classic.  Writer/director Amy Heckerling turns Jane Austen’s Emma into an addictive and heartfelt tale of high school relationships and finding one’s impact on the world around them. Alicia Silverstone’s Cher is a pitch perfect heroine whose big heart is only outmatched by the size of her closet. Heckerling’s loving wit doesn’t just apply to our leading lady. The entire high school is filled with big personalities (and bigger wallets). One of my favorite characters has always been Christian (Justin Walker), an old soul who becomes the first (and likely not last) gay man that Cher falls for. 

While mostly a supporting player, Christian isn’t solely defined by his sexuality. He gets to be a fully rounded connoisseur who seamlessly moves from a romantic interest to a gay best friend...

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