Even if you know which which of the big acts you want to catch at Outside Lands — Twenty One Pilots or the Lumineers (or Flying Lotus!); Childish Gambino or producer RL Grime; and Paul Simon or Kygo—you’ll be making important choices all day long. The modern music festival is a choose-your-own-adventure experience. Every hour of every day between Aug. 9 and 11, concertgoers will be having to decide between the top up-and-comers in every genre with established acts and future Rock and Roll Hall of Fame inductees.
Don’t forget the food, wine, shopping, comedy and cannabis. I’m somewhat ashamed (and somewhat proud!) to admit I’ve gone an entire day without worrying about relieving myself. I’ve also gone days where I took one look at a porta-potty and turned right around. That’s a different column, though.
Every year I lead the RIFF team in coordinating which acts we’re going to cover. Even with two teams covering overlapping stages, we only get around to half of the music—this is also unrelated, but RIFF has the most thorough music coverage from Outside Lands than anyone and I’m tremendously proud of that. Bookmark this site and come back each night to read about the highlights and see some amazing photography. We literally stay up until 5 a.m. to bring you this stuff.
Where was I? Oh yes, lineup conflicts. The editorial staff put their heads together to come up with these hour-by-hour music recommendations.
The second weekend of August in Golden Gate Park smells best in the morning, and the best-smelling morning is Friday. Blow off work and arrive before gates open to be among the first in the park. If you’re in right away, you have your choice of lunch without waiting in line. My own personal favorite is Pica Pica Arepa Kitchen. Take the time to walk around and learn your surroundings because a few hours later, it’ll all be one big dust storm.
12 to 2 p.m.
The first music decision for us is between Taylor Bennett, the talented younger brother of Chance the Rapper, and SoCal folk trio Rainbow Girls. Considering that Bennett is at the Land’s End stage and Rainbow Girls are at the smaller Panhandle Stage—a 10-minute walk without traffic—you probably don’t want to start using your tank of energy to catch both. After either set, make your way over to Land’s End to catch Long Beach alt-pop trio half•alive.
2 to 4:30 p.m.
Every year, some artist attracts such a large crowd to the tree-lined Sutro Stage that there’s not even any standing room with a sightline to the stage. Could that artist be Cautious Clay in 2019? The multi-instrumentalist and producer will be playing everything from guitar to the saxophone and his first instrument, the flute. He’s impressed everyone from Khalid to John Mayer so chances are that you’ll leave his set happy, too. When you’re ready, make your way back to Land’s End to catch the end of P-Lo‘s set. The rapper is a member of the Hercules-based HBK Gang, which includes Iamsu! and Sage the Gemini, and used to include Kehlani. Then, you have the opportunity to enjoy your first cross-grounds walk to the Twin Peaks Stage, which at this point will take you about 15 minutes. Walk through the woods and pick up some chocolate along the way for your trouble. The big reward will be Scandinavian alt-pop songstress Aurora.
Note: if you’re not up for the long walk, which you’ll have to repeat, hang around the Land’s End stage for The Neighbourhood.
4:30 to 8 p.m.
Here’s a big one, and you likely don’t even realize it. In the blue corner (Land’s End, if you’re going by the Outside Lands website’s color scheme), you’ve got Lil Wayne. The rap legend and living meme is well-known enough to not need a reason from me to see him. But in the black corner (Twin Peaks), you’ve got Lauren Daigle, who’s a smashing success on both pop and Christian radio. Lucky for you, we’ve got teams at both, so whoever you miss, you can read about after you get home. Adding salt to the wound, Masego is performing at the same time, but he’s played the Bay Area recently. Hopefully you caught him at Sol Blume in Sacramento.
At this point, you’re going to tell your friends that you’re gonna go and discover Yaeji, but you will undoubtedly end up at Blink-182 at Land’s End. Who knows, maybe Lil Wayne will show up. And is Blink-182 is too hip and modern for you, take another five-year step back in time with the Counting Crows at Twin Peaks. If both are before your time, you’ll likely end up trying to get close enough to see something to electronic artist Han Solo at the Sutro Stage.
8 to 10:30 p.m.
This brings us to the headliners, which on Friday comes down to taste. The Twenty One Pilots crowd will be younger. The Lumineers crowd will be older. Flying Lotus will draw a sizable crowd for whom both of those other acts aren’t hip enough. Believe it or not, this is the easiest choice you’ll have to make.
12 to 3 p.m.
The first day usually hits me pretty hard by Saturday morning. We have to be ready to go on just a couple of hours of sleep. You don’t, so it’s a good opportunity to sleep in. But if you’ve got the stamina, you should start either with hip-hop artist Felly at Land’s End or soulful songstress Fatai at the Panhandle stage. Either way, make your way afterward to Twin Peaks for Oakland rapper ALLBLACK (on this our editorial board agrees wholeheartedly). If you leave his set a little early, you can catch a bit of pop artist Delacey as you make your way to see alt-rockers Wallows at Land’s End.
4 to 6 p.m.
If you’re already at Land’s End by now, you’ll be hard-pressed to skip Santigold, who’s up next. But just as enticing is Tierra Whack at Twin Peaks (which by this time is a 20-minute walk through packed bodies). If you went to Sol Blume earlier in the year, you probably saw Tierra Whack already, making your choice easier.
At this point you’ve got a difficult choice among two future pop divas in Alina Baraz and Bea Miller, electronic act Big Wild and folky band Phosphorescent. Sure, they’re gonna play “Song for Zula,” but how long will you have to wait for it? Our suggestion is to choose one of the first three.
6 to 10 p.m.
Time for the homestretch. Electronic act Flume is the top 6 p.m. draw, but if you’ve gotten your fill of dropped beats, may we suggest kinky-mouthed rapper CupCakKe at the Panhandle? This is sure to be one of the most unique performances at Outside Lands. If you brought any inflatable phalluses, you’ll be waving them around here.
Next make your way back to Twin Peaks for pop hitmaker Ella Mai and to Sutro to watch Hozier sing “Take Me To Church” from afar. To finish off the night, I’d pick Childish Gambino. Of all headliners, he’s the most exciting to me. I remember interviewing Alison Brie, his costar on Community, a few years ago. She just gushed about his singing and rapping abilities. She was right. But we’ll also be at RL Grime.
12 p.m. to 2:30 p.m.
Traditionally, Sunday at Outside Lands has kicked off with a gospel or soul music set, and this year you’ve got a couple of soulful choices, either with Levin Kali at Twin Peaks, or the double shot of R&B vocalist (and Maroon 5 keyboardist) PJ Morton and Mavis Staples at Land’s End. Staples had one of the all-time best performances at Outside Lands a few years ago, complete with an appearance by Arcade Fire’s Win Butler. Who knows, maybe Hozier will make an appearance this year, as the two collaborated on his new album? What I’m trying to tell you is that you should come ready to fill your soul with the good news.
2:30 to 5:40 p.m.
After Staples, saunter around the bend to catch the first half of Dean Lewis‘ set at the Sutro Stage. Lewis may not be a household name yet in the U.S. but the Aussie melodramatic crooner is close, and you still have a chance to get in near the ground floor. Then run back to Land’s End for Judah and the Lion, who will have one of the most action-packed sets of the weekend. Even if roots rock and bluegrass ain’t your thing, come anyway because the band blends elements of punk, hip-hop and even electronica into its mix. Stay for the whole set.
Next, if you have any gas left, make the cross-fest hike to Twin Peaks for rapper Denzel Curry. If you already caught him in one of his Bay Area appearances over the past year (most recently opening for Billie Eilish), this is a good chance to catch some grub or take in a set at the Barbary comedy tent or GastroMagic for a cooking demonstration with a special guest. If you want some hip-hop, but Denzel Curry’s not edgy enough for you, you really need a long walk at the beach (or you can just wait a bit because Curry’s followed by Sheck Wes. Now, listen carefully: If you stay for both of the hip-hop sets at Twin Peaks, you’re going to miss not only country queen Kacey Musgraves at Land’s End but terrific electronic duo Bob Moses at Sutro. I’m not telling you what to do. It’s a Sophie’s Choice (but with, like, less death).
5:40 to 9:35 p.m.
For this next time period, let’s presume that if you’re a fan of Toro y Moi, you’ve already seen Chaz Bear’s project over the past 12 months, because I’m about to suggest you sacrifice it in favor of the first half of R&B crooner Leon Bridges‘ performance at Land’s End and the majority of pop-tart Bebe Rexha‘s set at Twin Peaks. I know, I know. You’re thinking, “You want to send me away from the main stage mere minutes before Paul Simon takes the stage. But look at it this way: If you take my advice to see Rexha, you’ll likely have more fun with production duo Funk Hunters at Panhandle and Twin Peaks’ night closer Kygo anyway.
And of course, if you skip Rexha, this is your last chance to grab a bite and wait patiently for Paul Simon to take the stage.
Follow editor Roman Gokhman at Twitter.com/RomiTheWriter.