Beyond the Hook Up: Cinema’s Hardest Working Wingmen

By Annie Cooper

Every pilot knows that flying a solo mission is twice as dangerous as flying with a partner. The same holds true in the high-stakes dogfights that take place in the world of dating. That’s why it’s wise to travel in pairs.

The wingman archetype we’ve become used to is the standard “guy-who-helps-another-guy-hook-up-with-girls” formula, but the duties of an apt wingman can be much more nuanced than that simple definition suggests.

Look at the relationship between Tom and Andy in KoldCast TV’s comedy series Gregory Way. Tom, a gay man at the beginning of an awkward mid-life re-invention, has taken the young, straight and single Andy on as his assistant.

Andy is an obnoxious, opinionated partyboy whose uncouth, unedited personality seems like it would be less than helpful to sensitive, high-strung Tom. But by bluntly pointing out the absurdities, contradictions, and stereotypes with which Tom is struggling, Andy, in his own ham-fisted way, is acting as the wingman Tom never imagined he needed.

You are watching Episode 1 of Gregory Way, “World Without a String”

Tom Gregory grew up always imagining himself as a famous movie star, but life got in the way and Tom ended up falling in love with the man of his dreams, rich business tycoon and technological entrepreneur David Bohnett. Now, Tom finds himself heading into the second half of his life and decides it’s time to make some changes. He decides to open up his own art gallery just down the street from his house and meets a young flashy would-be assistant Andy, who has a flair for danger and lack of authority. Tom hires him in the hopes that his lewd womanizing behavior might rub off a little bit on Tom and not make him so ‘gay”. The two love to egg each other on, and if Andy could have his way all the time, their life would be nothing but girls, parties and road trips to Vegas!

Watch Episode 2 and Additional Episodes of Gregory Way

Some of TV and movies’ greatest wingman relationships share this same complexity. A wingman needn’t simply be someone who helps you win a one night stand; he, (or she, or it), might just be someone who helps you win at life.

Jack (Sideways)

A “last hurrah” bachelor fling is the ostensible reason for Miles and Jack’s wine tasting excursion to the Santa Ynez Valley. Miles, played by Paul Giamatti, will act as affable backup while Jack, the ineffable Thomas Hayden Church, sows some wild oats before his upcoming wedding. In exchange, Miles will mope about his disappointing writing career in a beautiful setting, tasting wine and making disparaging statements about unsuspecting grape varietals.

But exactly who is whose wingman, here? Church’s performance as the sleazy, despicable Jack is exemplary of a particular type of wingman – the one who inadvertently makes you look good by being so completely awful himself. It works, since we’re led to believe that Paul Giamatti’s Miles gets the girl in the end, while all Jack gets is a well-earned motorcycle helmet to the schnoz.

Michele Weinberger (Romy & Michele’s High School Reunion)

Of all the social situations one will face in his or her late twenties, none looms larger or more ominously than the high school reunion. As far as I know, there are only three reasons to subject oneself to this unique form of torture: to flaunt your successes in the prematurely aging faces of your former peers, to bask in the glorious schadenfraude that comes with the proof that the mighty do indeed fall, and fall hard, or to hook up with an old crush who has recently changed his or her Facebook relationship status to “single.”

Regardless of your reasons for attending, the smart reunion-goer does not go it alone. And no one could pick a better wing-gal than Michele, played by Lisa Kudrow. She joins insecure Romy (Mira Sorvino) in her efforts to build a more impressive life, even though she’s fairly sure their life is pretty fun as it is.

Michele goes along with Romy’s scheme to pass herself off as the inventor of Post-It notes and even though Romy hurts her feelings by insinuating that Michele’s not smart enough to have invented sticky-backed paper, she defends Romy to the cruel “in-crowd” when her story is revealed as a lie.

Most importantly, Michele possesses the uncanny ability to include others as she improvises an elaborate interpretive dance to Cyndi Lauper’s “Time After Time.” I’m really not sure what more you could ask for from your wing-gal, honestly.

Sebastian (The Little Mermaid)

The relationship between human and crab is among the most sacred, especially when that human is a former mermaid princess and her crustacean caregiver is of the singing, Jamaican pursasion. Sebastian is more than Ariel’s guardian; he goes to great lengths no other wing-crab should even dare.

In order to ensure that Ariel is unharmed in her foolhardy quest to become a human, he lays his delicious little self on the line, risking life and claw at the hands of a psychotic chef. Against his better logic, Sebastian eventually ends up helping orchestrate the budding romance between Ariel and Prince Eric, proving he’s a soft-shelled crab at heart.

Maverick (Top Gun)

You thought I was going to say Goose, didn’t you? That’s the easy answer, but everyone knows that any wingman worth his salt doesn’t eject from your F-14A Tomcat and die halfway through the movie, leaving you to question your fundamental life choices.

No, the real wingman here is Maverick himself, and the beneficiary of his smooth aerial maneuvering is none other than the United States Navy. Tom Cruise’s performance in Top Gun did more for Navy recruitment than all their slickly-produced TV spots combined. And this isn’t just a presumption. The US Navy itself reported that enlistment spiked by 500 percent following the film’s release. Talk about a return on investment.

Considering the film was released in 1986, it can safely be assumed that there are countless high-ranking pilots, instructors, and commanding officers out there right now who continue to proudly and bravely serve our country, simply because when they were 17 they thought a stint in the Navy might give them a decent shot at Kelly McGillis.

Annie Cooper is a writer, armchair public transportation advocate, and aspiring taco critic. She has written columns and specialized training materials related to children with special needs, parenting issues, and early childhood development. She recently left her job in social services in an effort to become part of the problem, rather than the solution. Annie lives in Los Angeles, but she’s not from there – nobody’s from there.