Zack O'Malley Greenburg's Blog

Bad Bunny's Super Bowl Gig: A Classic Jay-Z Audience Swap

Yesterday, during a commercial break on NBC’s Sunday Night Football broadcast, a closeup of Bad Bunny’s face appeared, panning out to reveal him seated on a beachside goalpost. When “FEB 8” flashed across the screen, the message was clear: the Puerto Rican superstar had been selected to headline the halftime show of the upcoming Super Bowl.

“What I’m feeling goes beyond myself,” Bad Bunny said in a statement. “It’s for those who came before me and ran countless yards so I could come in and score ...

What Would Jay-Z Do: Buy The Whole Car

This is the second installment of the series “What Would Jay-Z Do?” He once said he’d give you $1 million worth of game for $9.99. I’m offering it for even more of a bargain: the price of a Substack subscription. As the author of the Jay-Z biography Empire State of Mind, I know a thing or two about the guy. Enjoy!

Toward the end of “Can I Live?”—the mellowest and perhaps most under-appreciated song on Jay-Z’s epic 1996 debut, Reasonable Doubt—the rapper offers some lyrical financial advice: “We d...

Greening Live Music In The Age of Trump

It’s less than an hour before the Dave Matthews Band takes the stage on a sunny Thursday evening on the coast of Long Island—but the biggest crowds at the Northwell at Jones Beach Theater aren’t at the tequila bar. They’re in the “eco-village” operated by Reverb, a nonprofit focused on greening live music by inspiring fans to take action around climate change.

As I wander through tents emblazoned with the logos of organizations like the Nature Conservancy and Generation180, volunteers explain how...

Taylor Swift And The Live Music Slump

I’ll never forget my first big concert—Pearl Jam, Madison Square Garden, 1999—and, with similar fondness, I’ll always remember my initial show after the Covid-19 lockdowns during the “Hot Vax Summer” of 2021. The artist was Brandi Carlile, the venue was Forest Hills Stadium, the afterparty was near the pool in the back. By the end of the night, just about every remaining reveler ended up in the warm, generously chlorinated water.

The next couple of years resulted in record numbers for the live mu...

What Would Jay-Z Do: Argue With Fools

This is the first installment of the series “What Would Jay-Z Do?” He once said he’d give you $1 million worth of game for $9.99. I’m offering it for even more of a bargain: the price of a Substack subscription. And, as the author of the Jay-Z biography Empire State of Mind, I know a thing or two about the guy. Enjoy!

“A wise man told me, ‘Don’t argue with fools, ‘cause people from a distance can’t tell who is who,’” Jay-Z once rapped. At various points during his rise, he used the parable to his...

A Coda For My Musical Mentor

On a Wednesday afternoon in late March, my uncle James O’Malley sat smoking a cigarette in his backyard on the outskirts of Austin. His cowboy hat was tilted low over his sunglasses, and he cracked jokes as a light breeze stirred the wind chimes. If you didn’t notice how skinny he’d gotten under his faded purple shirt, and if you hadn’t seen how much effort it took him to get into his wheelchair that morning, you could almost pretend he wasn’t dying.

About a week earlier, James had decided to shi...

Introducing "What Would Jay-Z Do?"

Back in 2011, Jay-Z and Kanye West released “Otis,” the lead single from their collaborative album Watch the Throne, packing it with terms that quickly became part of the vernacular. Among them: “luxury rap,” “new watch alert,” and “my other other Benz.”

My personal favorite was Kanye’s line, “Maybach bumper sticker read ‘What Would Hova Do?’” I liked it so much that I designed an actual bumper sticker with the slogan on top and the URL to buy my Jay-Z biography Empire State of Mind underneath. T...

Diddy's Diminished Net Worth

My story on Puff Daddy’s evaporating empire was originally published in Fortune earlier this winter. In case you missed it, here’s the full piece.

In 2022, several decades into a storied entertainment career, Sean “Diddy” Combs’ star—and his net worth—still seemed to be rising. He had hosted the Billboard Music Awards, launched a new record label, and attained billionaire status.

Since then, however, federal racketeering and sex-trafficking charges and a cascade of civil lawsuits have scuttled so...

Music Streaming Surprises

The Grammys and the Super Bowl are over, and we’re already halfway through February, a little late for a 2025 predictions piece. But as we await the melting of snow and the beginning of baseball season, it seems like a good time to delve into the biggest streaming surprises of the last year, and beyond.

So I teamed up with my pal Dan Runcie at Trapital to dig into a trove of data—Luminate’s 2024 Year-End Report and the all-time Spotify numbers, which now span nearly two decades—you can listen to ...

Best Bets For Grammy Glory 2025

Last year, taking a cue from oddsmakers, I predicted Taylor Swift would sweep the three top awards at the Grammys. She did capture Album of the Year for Midnights, becoming the first person to win that honor four times. But Swift fell short in Song of the Year (“Flowers” by Miley Cyrus) and Record of the Year (“What Was I Made For?” by Billie Eilish and her brother, Finneas).

Going one-for-three your whole career might make you a baseball Hall of Famer; however, it’s a decidedly subpar mark as a ...