Our Editor in Chief dug deep into his Grammy crystal ball—and even deeper into his stash—to deliver his predictions for the Top Four Grammy categories. Feel free to play along at home, but pace yourself on the weed. Lenny is a professional.

RECORD OF THE YEAR

Childish Gambino, “Redbone”: This is my personal favorite—the most interesting and unique single of the year. It’s a brilliant throwback to the psychedelic funk/R&B of the early ’70s, mixed with a healthy dollop of Prince. And creator Donald Glover’s achievements as a multimedia creator are indisputable. Even so, it’s probably a longshot in this category.

Luis Fonsi & Daddy Yankee fJustin Bieber, “Despacito”: The record was a monster even before there was an English-language version, and with Bieber on board, this remix altered the pop landscape. It was inescapable and swept up listeners of every stripe. One of the biggest records of all time—and the clear favorite.

Jay-Z, “The Story of O.J.”: Jay gets major props from the Recording Academy for his stature as a hip-hop trailblazer, statesman and industry mover. And this is certainly an interesting and timely record. But he’s unlikely to take this trophy.

Kendrick Lamar, “HUMBLE.”: This smash from Lamar’s streaming giant DAMN. is unquestionably a powerhouse, and shows hip-hop’s most inventive star at the top of his game. This is probably the second favorite, but so far we haven’t seen Grammy voters support Lamar in the top tier. It seems more likely that he’ll be rewarded in the Rap categories.

Bruno Mars, “24K Magic”: Mars is one of the most riveting entertainers of his generation, and his pop-funk alchemy is in fine form on this infectious party jam. But it’s not quite as undeniable as some of his prior work.

Will win: “Despacito”
Dark horse: “Redbone”

SONG OF THE YEAR

Luis Fonsi & Daddy Yankee, “Despacito”: For the reasons cited above, it’s hard to believe this ubiquitous Latin behemoth won’t win this category as well—it’s the biggest and the best. (Writers: Ramon Ayala Rodriguez, Justin Bieber, Jason Boyd, Erika Ender, Luis Fonsi and Marty James Garton Jr.)

Jay-Z, “4:44”: Jay’s multiple awards are a crowning achievement to an extraordinary career and, again, a measure of profound respect from the industry. But this one is not a contender. (Writers: Shawn "Jay-Z" Carter and Dion "No I.D." Wilson)

Julia Michaels, “Issues” The tunesmith-turned-artist has undeniable songwriting chops, and this song had a breakthrough run. It could be a sleeper with Grammy voters who love her. (Writers: Benny Blanco, Mikkel Storleer Eriksen, Tor Erik Hermansen, Julia Michaels and Justin Drew Tranter)

Logic f/Alessia Cara & Khalid, “1-800-273-8255”: This is the first song MTV has broken in the last decade and maybe longer, exploding after Logic’s VMAs performance. The suicide-hotline anthem has a clear, important message and must be considered a contender. (Writers: Alessia Caracciolo, Sir Robert Bryson Hall II, aka Logic, Arjun Ivatury, Khalid Robinson and Andrew Taggart)

Bruno Mars, “That’s What I Like”: Bruno is a monster, but why were two separate tunes of his nominated for Song and Record? This one isn’t likely to go the distance. (Writers: Christopher Brody Brown, James Fauntleroy, Philip Lawrence, Bruno Mars, Ray Charles McCullough II, Jeremy Reeves, Ray Romulus and Jonathan Yip)

Will win: “Despacito”
Upset surprise: “1-800-273-8255”

ALBUM OF THE YEAR

Childish Gambino, “Awaken, My Love!”: This probably falls under the “thrilled to be nominated” category. A progressive, interesting and bold set, but not a real contender

Jay-Z, 4:44: The frontrunner as a combination lifetime achievement award and a powerful statement from a mature artist—and a way for Grammy to pick a rap record and not give it to Kendrick.

Kendrick Lamar, DAMN.: The L.A. rapper has so far not fully won over Grammy voters, despite dropping an album that was both the year’s most acclaimed and a giant smash. He has banked much respect, but the top-tier categories have eluded his reach—can he surmount mainstream resistance?

Lorde, Melodrama: The Kiwi artist owned the cool market and unquestionably took a big step forward creatively with her sophomore full-length. But her nomination here was a longshot; it’s a year for hip-hop to win.

Bruno Mars, 24K Magic: He touches every base and it wouldn’t surprise us if he won—he’s Grammy Whisperer Paul Grein’s choice for Album. Again, though, the vibe of the moment strongly points to a rap record taking the prize.

Will win: Jay-Z
Should win: Kendrick Lamar

BEST NEW ARTIST

Alessia Cara: This is the makeup for her not getting the nod last time. What’s more, the well-respected singer/songwriter’s second year in the limelight was even better than the first, as she bolstered her credibility as a solo artist and established herself as a feature VIP. She could be here for the long haul.

Khalid: The young artist/songwriter—whose 20th birthday will fall shortly after this year’s ceremony—is part of the new R&B movement: part throwback, part progressive. He’s built momentum throughout the last year and is extremely well-liked.

Julia Michaels: People fell in love with this pop thrush’s talent and personality, as she stepped from the writing room to the stage. But she hasn’t yet extended her own success beyond one hit (though she’s penned plenty for other acts). When that happens, she could go all the way.

Lil Uzi Vert: The inclusion of this rapper seems like the Academy’s sop to streaming, since he was frequently spotted atop the Spotify and Apple Music charts as both main artist and feature. He’s a longshot, to say the least, in this category.

SZA: This R&B trailblazer, who made my favorite album of the year, is certainly the favorite. In terms of songwriting depth, expressive vocals and galvanizing point of view, her Ctrl is the most potent album of its kind since the arrival of Lauryn Hill. In a category that’s been a constant source of surprises, I’d be surprised if she didn’t win.

Will win: SZA
Could win: Alessia Cara