In a music genre associated with crime and "street cred", do Drake's soft-spoken lyrics and public love-life feel out of place?
With each passing album, the Hotline Bling singer feels to me more like a pop star and less like a rapper.
With the Saturday release of his album/playlist More Life, the former Degrassi teen actor seems to have got back on the critics' good side, but scrutinising his love misadventures won't help his street credibility.
After years crying over a failed relationship with Rihanna, Drake is now addressing his supposed fling with Jennifer Lopez, by describing a scene where she purposely changes numbers to avoid his texts.
"I drunk text JLo, old numbers so I bounce back, Boy Wonder gotta bounce back."
He doesn't stop there, though, sampling the chorus of JLo's If You Had My Love in another song, including lyrics like: "You're to blame for what we could have been, 'cause look at what we are."
This seems too much like the rapper's 2016 collaboration with former girlfriend Rihanna, complaining that "the only time you see me, is when you turn your head to the side and look at me... differently".
His reputation of being a "soft rapper" is nothing new and his confessional-style lyrics have earned him his current fan base, but Drake has found himself often defending his choices.
A few years back, in a Guardian interview, the singer addressed criticism by saying he is just "not one of those people who's closed off emotionally".
Adding to his "bad cred" are unfortunate episodes which include a fight with Chris Brown over Riri and a feud with Meek Mill over not writing his own lyrics - none of which Drake has exactly left on top.
In 2014, the internet reacted in a bullying way to a video of the singer caught lint rolling his pants courtside at an NBA game, inspiring the Toronto Raptors to handout Drake-branded lint rollers.
Again, not great if you're trying to follow the footsteps of Biggie Smalls or Rick Ross.
But, then again, maybe Drake isn't.
By finding a new voice and "getting in touch with his feelings", the Toronto-born singer has built a niche, while still managing to collaborate with some of the best rap being produced today.
More Life draws clear inspiration from his travels around the UK, and his support for Grime artists and Brit rap are smart moves for Drake.
His so-called "people in Leeds" include big names like Skepta and Giggs.
These are very different vibes from the "thoughts too deep to go work 'em out with a therapist" lyrics of his past album.
Maybe Drake's honesty, his refusal to be labelled, to stick to one genre and to fall into stereotypes are the secret ingredients which make him the international success that he is.
At this year's Grammy Awards, Drizzy won best rap performance and best rap song for Hotline Bling, and his reaction was indicative of his market placement .
"I won two awards but I don't even want them cos it feels weird for some reason. It doesn't feel right to me," he said.
"I feel almost like alienated or you're trying to purposely alienate me by making me win rap awards, or either just pacify me by handing me something, putting me in that category, cos it's the only place you can figure out where to put me."
Maybe the reason why Drake's rap feels soft is that it isn't rap at all.
For now, reviews for his playlist have been favourable, and some even predict a Sheeran-styled charts rampage come next week.