Over the last two years I’ve developed quite a relationship with Drake’s 2011 sophomore album, Take Care. At its best, Take Care is a thoughtful, inward-looking account of fame and youthful indulgence.  At its worst, its the prototype for the next decade of Hip-Hop, combining classic R&B tropes, with radio-ready singles.

Drake would have been okay without Take Care. While 2010’s Thanks Me Later falls short musically, the actor-turned-rapper rose to A-list prominence through a series of well connected verses and a close association to veteran, Lil’ Wayne and fellow A-list newcomer, Nicki Minaj.

Take Care will probably be remembered as the “sad club music” album. Its casual shift in tone from vulnerability to bombastic excess and back is revealing. Listening to the album from beginning to end, you can really start to understand Drake as Aubrey, and Aubrey as Drake.

Take Care could have easily been an album about the perils of success or going to crazy parties with models. But by making it about both, Drake invites us to learn with him. He’s not without flaws. There’s an argument to be made that Take Care is a purposely half-hearted attempt to hide those flaws. Ultimately, people are way more interesting when they have something to hide, and Drake provides context to massive fame and wealth. The club is way more fun when you’re escaping something else.

This isn’t the only way to read Drake, however. In fact, this may not even be the way Drake reads Drake. He does a lot of cringe-worthy things for someone so obsessed with appearance. His aesthetic hodge-podge could be read as an attempt at mass marketing or it could be the result of someone who isn’t exactly sure how he wants to be portrayed. The same guy who wrote “Marvin’s Room,” ghost-rides a white Bentley dressed in all white as snow flutters down upon him in a music video in 2013. These sorts of things make it tough to defend Drake as a maker of art that is good instead of a maker of anthems that are played in between Pitbull songs. For every thoughtful, crafty decision, he also makes a lot of ridiculous 2nd-hand embarrassment-inducing career choices.

Whether he meant to or not, his two sides—the purposeful, smart Drake and the over-compensating-rapper Drake—have successfully made him into the biggest, and most dynamic artist on the planet. The rapper’s struggle to define his own style and position in the hip-hop canon has actually worked to his advantage, and instead of pigeon-holing himself into one category, Drake has picked up fans from all corners of the hip-hop landscape. But again, this is, in a way sort of accidental. He’s still the number-one punching bag in the rap game, and as a result, has beefed up the bombastic, self-loving lyrics leading up to his forthcoming album, Nothing Was the Same.

Practically every song Drake has released in 2013 has been a radio-ready hit. As ridiculous as the premise to “Started from the Bottom” may seem, it’s a phenomenal song. Leading up to the September release date, Drake has adopted an “us vs. them” attitude, which is only partially ridiculous. Here we have the most popular artist in mainstream pop culture rallying behind the idea of having no new friends, as if, people are actually seriously trying to mess with him. Being the softest rapper in the game probably sucks a lot worse when you’re not winning Grammys and selling out arenas. He is somehow having his victory lap with a chip on his shoulder.

It’s not so much as an image problem, because calling it a “problem” would mean it isn’t working. Whatever it is, one thing we do know is that it is working, in a sense that his popularity has soared. Drake is by all accounts trying to be a rapper. Is he trying too hard? Probably. Is it working? Definitely.

As an audience, we don’t really need Aubrey Drake Graham to be hood. That’s not what we click play for. It’s obviously not my call to decide how the man should portray himself, however its very difficult not to get the sense that this is a man juggling a few different images. That’s probably what makes him compelling, whether or not he knows that.