Outside Lands lineup: Here’s who we think will headline in 2020

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Not long after the last Outside Lands Music and Arts Festival ended in August, music lovers started talking about the next one.

And, not surprisingly, the topic revolved around the possible headliners.

Fast forward six months and the chatter has only grown louder, as fans hotly anticipate the release of the lineup.

We’re probably still several weeks away from the lineup being announced. (Last year’s card was announced March 26 and the 2018 bill hit on April 3.)

But that’s not going to stop me from looking into my crystal ball and trying to predict the names we might see headlining the 2020 Outside Lands, which runs Aug. 7-9 at Golden Gate Park in San Francisco.

I’ll start with the surest bets and work my way down to the long shots.

For more information, visit sfoutsidelands.com.


Likelihood: 90 percent

Previous OSL appearance: 2018

Following her phenomenal 2019, this amazing soul singer now ranks as one of the most popular artists in all of music and she’s already signed on to headline the big Bonnaroo festival in June. Plus, she’s already seemingly got a strong relationship with local promoter Another Planet Entertainment, having played Outside Lands in 2018 and followed up with two sold-out nights at the Bill Graham Civic Auditorium last year. So, I fully expect to see Lizzo’s name atop the bill when it’s finally released. She’d be a great Saturday headliner.


Likelihood: 70 percent

Previous Outside Lands (OSL) appearance: 2010

I thought we might get these garage-rock revivalists last year, but now it appears I was one year off. The fact that they announced a string of West Coast/Pacific Northwest dates for March, but didn’t include the Bay Area in the bunch, only strengthens my view that the Strokes are coming to Outside Lands in 2020. And the band would be a cool Friday headliner.

Travis Scott

Likelihood: 65 percent

Previous OSL appearance: None

This would be a huge booking for Outside Lands, one that would motivate thousands of fans to snatch up those three-day passes. Scott is definitely open to playing festivals – such as Southern California’s Coachella, which he’ll headline in April – so why not sign the contract and make his long-awaited debut at Outside Lands. He would make a great Friday or Saturday night headliner.

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Vampire Weekend

Likelihood: 60 percent

Previous OSL appearance: 2013

It’s been seven years since their last showing at the festival, so it’s definitely time for a return to Outside Lands. Plus, Vampire Weekend is already signed up to do Governors Ball and Bonnaroo so why not add one more.

Lana Del Rey

Likelihood: 55 percent

Previous OSL appearance: 2016

Given the 2019 that she had – which included releasing the best album of the year in “Norman (Expletive) Rockwell” – Del Rey has certainly risen to the place where she should be headlining major festivals. It hasn’t happened yet. But maybe Outside Lands is the place where it does.

Missy Elliott

Likelihood: 45 percent

Previous OSL appearance: None

She’s signed on for Governors Ball in New York and we’re really hoping that she decides to play a big festival on this side of the continent as well. And the best fit would probably be Outside Lands. And would Missy – at this point as in her career – actually work in the “legacy headliner” role (see below)? I’d be down with that, for sure.


Likelihood: 40 percent

Previous OSL appearance: None

It gets really tricky when trying to figure out who organizers will slot as Sunday’s legacy headliner. And that’s because Outside Lands has just been so awesomely unpredictable in filling it during past years. I mean, who could have predicted Lionel Richie (2016), Janet Jackson (2018) or, especially, Paul Simon (2019)? I’ve been thinking Aerosmith, however, since they have a break in their schedule in early August.


Likelihood: 35 percent

Previous OSL appearance: None

Seems like a natural match. But it doesn’t feel all that likely for 2020, given that the legendary guitarist already played two big Bay Area shows — at Shoreline Amphitheatre at Mountain View and Chase Center in San Francisco — plus the BottleRock Napa Valley festival in 2019.

Diana Ross

Likelihood: 30 percent

Previous OSL appearance: None

Just love the thought of Ross leading tens of thousands of backup singers (aka, the crowd) through Supremes classics in Golden Gate Park.

Dead & Company

Likelhood: 25 percent

Previous OSL appearance: None

When the band announced its summer tour, minus any Bay Area dates, some people (such as me) started thinking that Outside Lands is a possibility. But the fact that Dead & Co. is performing Aug. 7-8 at Fenway Park in Boston makes a cross-country jaunt to play Outside Lands on Aug. 9 look like a real long shot.

Rolling Stones

Likelihood: 20 percent

Previous OSL appearance: None

Here’s the biggest wildcard of the festival. And if promoters can pull it off then it would truly be an occasion to remember for years to come.

Bruce Springsteen

Likelihood: 10 percent

Previous OSL appearance: None

I wish I could add another “0” to that percentage, because I’d love, love, love to be singing “Thunder Road” come August. But, The Boss just doesn’t seem like a festival guy to me.


Likelihood: 2 percent

Previous OSL appearance: None

Maybe that percentage is too high.


Likelihood: 1 percent

Previous OSL appearance: None

So, you’re saying there’s a chance? Well, no, not really.


Source: mercurynews
Outside Lands lineup: Here’s who we think will headline in 2020