How about this, if you had to sing the song you're thinking of covering in front of a group of non-white people would you feel comfortable, or uncomfortable?
“Call Your Girlfriend” - In its most innocent form, we’d call it sophomoric ignorance. If we’re being more direct, however, we’d call it dubious—at the very least—when a straight white male performs a song about a life which he has not lived and, by performing it, attempts to ingratiate himself with, and make himself sympathetic toward, the plight of the person who originally wrote it (Exhibit A is "911 Is a Joke" as sung by Duran Duran). Extending beyond racism, this issue becomes much trickier when it comes to straight males covering songs written by women, like with “Jolene” as performed by The White Stripes.
Now, I use "Jolene" purposefully here because, one, I like it, both the original and the cover, and, two, because the cover-er and the covered have similar enough backgrounds. But even with their commonalities, there’s an intrinsic problem, one where the straight man who's covering the song unknowingly, or, much more likely, knowingly, is putting himself in the corner of the woman who wrote it so as to be against those ‘other guys,’ the brutes who only care about looks and just want blow jobs and steaks and motor oil, or some combination thereof.
Before we go even further, let this be said: it's impossible to know who 'hurts' more. It could be that one group experiences more inner turmoil or it could be that we all feel exactly the same when love turns sour. Whatever the case, I can say from my own experience that watching a straight man covering "Call Your Girlfriend" seems very fake. Seeing his attempt to empathize with a woman’s pain, there's just something very "guitar guy at the party" about it.
And while this is only a guess, one may now be thinking, "This is music, buddy. This is art. Don't be so literal." So, as another clarifying statement, let me go on record and say I understand that music is not always meant to be taken literally. I get that it doesn't 'know' gender, creed, religion, sexual preference. But, I'm guessing, if your mind jumped to the sanctity of art, you're also someone who, before David Foster Wallace's biography came out, didn't think of him as someone who went on book tours for the intent of landing "audience pussy." So, for a moment, step with me out of fantasyland and into the reality that a vast majority of straight males who start a band do so because they want to have sex with members of the opposite sex who are more attractive than the members of the opposite sex they're used to having sex with. That's natural selection and if we want to start talking about how that's supposed to be taken less than literally, I have a museum in Kentucky that’s open year round.
Every Bon Iver Song - Even if you, aspiring straight white male singer/songwriter, complete your end game here of capturing the alt female of your dreams, the one who knits, gardens, has chickens in their backyard, you are still left with problem of being pigeonholed by her as, "the guy who does a really good Bon Iver voice." And the problem with that is this: the Bon Iver voice is not sexy. Sure, the Bon Iver guy made it sexy, for him, singing his falsetto poems about foxes in the snow or the Packers on Monday night or whatever, but crooning a full octave above your range about tree-forts is more than likely just not you. It's kind of like the wisdom your mom, maybe your dad, gave when it came to first talk with a girl. "Son, just be yourself."
Every Prince song - I have to imagine that most Prince songs would be difficult to cover. They’re not always the usual length ("D.M.S.R" and others), they don't always have metaphorical lyrics ('I sincerely wanna fuck the taste outta your mouth'), and often they don't have the kind of singing tailored for straight white males ("Purple Rain, etc)."
And now after reading that and knowing what this is all about someone might say, "Well, buddy, that's exactly the reason why my band is going to cover Prince. That's what music's about, taking it to the limit, not having boundaries." Of course, that's a nice thought, but if you put it into practice and insert Straight White Male Band A playing Prince song X, you start to realize why it's also a terrible one.
That said, I will admit this much, you can’t fault the straight white male for trying, especially with a song like "I Love U in Me," which I would pay to see Creed or Nickelback play, but, as a standard rule it's best for you, straight white males, to live by this motto, "I pledge to never cover Prince. I know it's tempting because I believe I'm different. But, from this day forward, I will push back all my misdirected desires to be funky."
Every Adele song - If you asked one, I would guess a straight white male musician would tell you that a song like "Someone Like You" speaks to all people and that it isn't just for a singer in England who was dating a music producer but was dumped after the music producer started seeing another woman, read: one who he believed was more attractive (which is, not so coincidentally, the reason all straight men ever start seeing someone else).
But not only is this cover a problem because we know everything there is to know about Adele, making it hard not to think of her when you hear one of her songs, it's also problem because, to say it quite simply, no one wants to hear an Adele cover, ever again. However, if you’re still feeling tempted, just say these words out loud, “I’m thinking of adding an Adele song to my set. It’s going to be really good.” It’ll hit you sooner or later.
Rap - Many straight white males in a band have a simple, though unavoidable and impossible to solve, problem. That is, they don’t have a ‘story.’ And while they can try and soup up their legend with allusions to the shaded meaning of triangles in their lyrics or to being bullied in junior high, they know, down deep, the darkest thing that ever happened (besides meeting at an intramural frisbee game in college) came after a gig in Sioux Falls when the drummer and bassist had a ménage à trois with a 17-year-old in back of the tour van. So, while they may dream of being considered dangerous in some way, sadly, for the straight white males, they're not of any kind of foreign descent, they don't party more or less than anyone else, and, often, they don't even have so much as one woman in the band. That is to say, they're blander than Arcade Fire, which makes them just about as white as, I don't know, Grizzly Bear, for example.
So then the best advice with rap is this, don't do it, straight white male. You may think you can pull it off but you can't and that's okay. As long as you aren't from Alabama or Utah, the rest of us will live under the assumption that you believe all people are equal. Sure, some songs actually might be okay, more pop-ish ones that don't have any context or language to give you away as a completely clueless, possibly racist, person, if you sung them. But covering that rap song you want to cover, even if it's commercial rap, when only make us doubt.
Though, now you might be asking, “but wasn't it neat when that guy did "Hey Ya?"” And sure, that was, kind of. But it's a slippery slope. From there, you might be asking “wasn’t kind of neat when Ben Fold's did that Dre song?” And then you might even be wondering, “wasn’t that Hack Dynamite song good?” You see the problem here?
How about this, if you had to sing the song you're thinking of covering in front of a group of non-white people would you feel comfortable, or uncomfortable? When you come up with the answer, this will all seem much simpler.
“Hallelujah” - This one would be forgivable to cover, though only if you've just arrived to earth via a space-time machine and while you don't understand modern technology like toasters and cars and podcasts about the hardships of being a comedian, as these are the only kinds of podcasts on earth, you are somehow able to use a guitar and sing. Otherwise, covering this song is unforgivably bad, bundling up "Wonderwall,” "These Days," and "Imagine" and singing them as a medley to a room of high school girls at youth group bad.
As for the rest of the cover songs to avoid, I won’t lie to you, straight white male, they’re out there, just waiting for one step over their, what once looked to you, thatched false ground. But, now that you’re a little older and wiser, you know better where to step. Or, at least, you know enough now that if decide to play one from the above, you’ll be able to remember back and play with the knowledge that anyone in the room - who has any brains - really thinks you’re an idiot.