Lil Wayne’s “Comfortable” Was a Kanye Song Ahead of Its Time

Day 342: “Comfortable” feat. Babyface – Tha Carter III, 2008

When people point to Tha Carter III as being an uneven album that fell short of Lil Wayne’s ambitions to make a classic, when they lament what could have been while holding up The Carter III leaks as a counterexample, they often point to this song, “Comfortable.” It is, admittedly, out of place. It is not Wayne rapping at a million miles per hour or pushing forward the weirdest free associative boundaries of human thought. It is wholly conventional. But even there, it’s not really a successful single, if that was the intention. It just is kind of a run of the mill, easy-breezy lightweight R&B fusion jam with Babyface. It is also, incidentally, one of my favorite Lil Wayne songs.

“Comfortable” is produced by Kanye West, and it bears mentioning that it came right around Kanye’s own pop peak, right in the wake of Graduation. But as I was listening to it last year, in the early days of A Year of Lil Wayne, I was struck by how much it had in common with Kanye’s production choices on The Life of Pablo. It feels fresh; it feels open. Time is a flat circle and all that, but it’s funny to imagine how different the reaction to this song might be were it to be released now, in the wake of 90s R&B’s critical revival and Kanye’s adult contemporary phase.

I maintain that it slaps and has always slapped, that it stands as the smoothest Wayne has ever sounded, that it is the rare moment where lines like “I could never one-two-three-four-get about you” and “I do confess to the murder scene / ’cause under those sheets I am a mess” actually work. Lil Wayne gets in not one but two Beyoncé punchlines. And Babyface sounds, as ever, immaculate. Is it a tragedy that Kanye and Lil Wayne, the two greatest hip-hop artists of their era, linked up at their respective heights to make, of all songs, this song? Many people would say yes, but that’s tired. The wired take is that this song is the ultimate smooth rap jam, and many secrets of human civilization are hidden within this work by some of the titans of modern music. Enjoy it in the context of music today, and I promise you will find it was ahead of its time.

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