'Round Midnight is said to be the most oft covered jazz standard in all the history of the genre. Chances are if you aren't familiar with the title, you've still probably heard the song in some capacity and by someone other than Thelonious Monk who is said to have composed it in 1940. It didn't originally have lyrics, but when they were added they told a story of deep longing in the late night hours. It's on some hugging-your-pillow-staring-outside-as rain-taps-against-the-window pane-and-sighing isht...with this song playing in the background, HAHA.
That being said, there are a couple of recent renderings of the song that I really dig. The first one is by Amy Winehouse, which appeared as a non-album b-side with the 2004 single "Take The Box" from her debut album "Frank." She wasn't even 21 when she recorded this, but her delivery was impeccable. She knew exactly what to put behind the notes she was singing to make them matter - I think we Black folk call that "soul." The overall production is great - quirky yet sultry, it definitely can get you to feel some kinda way if all the right elements are in place.
More recently, there's Jazmine Sullivan's live cover. She's straight outta the Black Lily scene in Philly, and getting her feet wet in the industry with the likes of Missy Elliot. There's not much I can really say to prepare you for the voice you're about to hear, so I'm just going to post the track. Give yourself about 5 seconds before you check your arm for goosebumps:
So yeah. I don't really prefer one cover over the other - they're both pretty badass in their own respects, so it doesn't do them justice to compare. It's just cool to hear how different people interpret the song and how they choose to convey it in their delivery.