Being A Great Wingman Is Like Being A ‘Featured Artist’


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Sure, in most states it’s “legal” to go to a club and meet women by yourself, but you’re better off bringing some company. Same goes for hip-hop music: life’s easier when you have someone helping you with your dirty work, whether it be counting cash, throwing cash or doing something else with cash.

That’s why if you look at the 2012 Video Music Award nominations for Best Hip-Hop Video, four of the five songs have more than one artist. Having a wingman, like having a featured artist, just makes sense. Here are four reasons why, based on the Best Hip-Hop Video nominees:

Both compliment your image.

Look, Drake‘s a good looking guy. We can all agree with that. Drake especially would agree with that. But Drake’s image is a lot like his haircut: nice and clean. And women like bad boys (thus the popularity of the movie franchise “Bad Boys“), so if you’re clean cut, it can behoove you to have a wingman with a little edge. Maybe a guy with long hair, some tattoos… maybe he did a little jail time. Drake knows what I’m talking about. It also doesn’t hurt to get a “Lil” guy either. Makes you look taller.

Both know your worst qualities.

Kanye West‘s life is awesome. Yours would be too if you had made the beat for “Izzo (H.O.V.A.)” But at some point, someone handed Kanye a microphone and he hasn’t been quiet about how awesome his life is since. A great wingman knows your weaknesses. For example: maybe you talk about yourself too much? On “Mercy,” three people jumped in to grab the mic away from Kanye. Hey, no one said you can only have one wingman. You should have as many as it takes to get the job done.

Both save your ass when you’re starting to look crazy.


Most guys know about “peacocking:” dressing to get attention with a crazy hairstyle or crazy clothes. But if you look too crazy (pink body suit, green hair, etc… Nicki Minaj, we’re looking in your direction), people will start to think you’re… well… just crazy. That’s when you need a wingman to step in and show people you have a normal side. Bring along your friend wearing a simple pair of True Religion jeans. Maybe he’s got some jewelry, but not too much… like maybe just 2 chains. Boom. You’re fun, not insane.

Both have as much, if not more, confidence than you do.

No one looks good hanging with scrubs who are beneath them. But what if you have confidence to spare? Like let’s say you’re the biggest rapper in the world. If you have a Jay-Z size ego, you need a wingman as big as Kanye West, because the only thing that makes you look awesome is hanging with someone who is equally as awesome. When your wingman is at this level of greatness, he no longer even has to don the “featured” tag. Hell, at this point, he may be the one that’s going to sleep with the chick you’re talking to. But hey, what can you do: it’s lonely at the top. Plus you’re married to Beyoncé . Go home to your wife and kid.

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Mike Pomranz (@pomranz) is a comedian, writer, musician and beer aficionado living in Brooklyn.