Lollapalooza | Festival preview

As thousands pour into Grant Park each August, Lollapalooza seems dominated more and more by newly emboldened teens and clothing-averse twentysomethings. Look a little closer and you’ll see older folks among the swell of youth, not just lazing in hammocks whilst sipping wine (yep, there’s a lounge for that), but doing laps back and forth past Buckingham Fountain. Those nostalgia acts aren’t just for Perry Farrell, after all. We surveyed the 128 acts playing across eight stages to break down the best route for you, whether you’re Gen X (black) or Y (red).

Friday 3
The first generation rift of the weekend arrives relatively early on. One of the most eagerly awaited (by Gen Xers, at least) reunions is the fest debut of the Afghan Whigs (Red Bull Soundstage, 4:15pm), whose menacing and firmly middle-aged fusion of soul and postpunk pulls in moms and dads from Kidzapalooza. Then tilt your body north toward the warm, folk-informed harmonies of the Head and the Heart (Sony, 5:15pm), which get a pop twist shortly thereafter from the Shins (Red Bull Soundstage, 6:15pm). At that point, faking heatstroke may be your best bet, in order to secure a golf-cart lift up north for the much-clamored about, almost all-original lineup of Black Sabbath (Bud Light, 8:05pm). Earlier in the day on the south end of Grant Park, Canadian synth-pop magnet Metric (Bud Light, 4pm) draws the Millennials before bizarro South African rap-ravers Die Antwoord (PlayStation, 5pm) blow the roof off what’s normally identified as the Petrillo Music Shell. From there, the youngs pivot slightly back north for the meticulous bubblegum confections of Passion Pit (Bud Light, 6pm) before hoofing it nearly a mile to new wave fetishist M83 (Sony, 7:30pm). Arena-blues champs The Black Keys (Red Bull Soundstage, 8:30pm) follow in their fifth turn at Lolla, though for the kids catching the group live for the first time, it might as well be Muddy Waters himself up there.

Saturday 4
By midday Grant Park is polarized once again. Chillwave messiah Neon Indian (Sony, 3pm) holds court for the Tumblr cognoscenti, as arty indie pulls the youngs in two directions: First to the playful synth daydreams of Chairlift (Google Play, 3:30pm), then back south for the pan-global deconstructions of tUnE-yArDs (Sony, 5pm). Up next is one of the biggest beneficiaries of blog hype, the Weeknd (Red Bull Soundstage, 6pm), whose dreamy, laptop-conceived R&B wafts across the sun-bleached masses, lulling those who aren’t buzzed on Red Bull into an afternoon siesta. Meanwhile, those who remember Web 1.0 start off the day with the seasoned, cross-country soundtracks served up by Delta Spirit (Bud Light, 2:15pm). From there, older heads crack open another brew and embrace the raw grooves of rock and soul reconstructionists Alabama Shakes (Bud Light, 4:15pm), catching a whiff of early aughties cool from Franz Ferdinand (Bud Light, 6:15pm), whose drawing power is cut into by the back-in-action Bloc Party (Sony, 7pm) on the opposite end. Many of the funk worshippers rallying around the Red Hot Chili Peppers (Red Bull Soundstage, 8pm) still remember the group’s Lolla debut two decades ago. The rest of us try to decide between the mercurial soul of Frank Ocean (Google Play, 8:45pm) and the chrome-outfitted pop constructions perfected by Santigold (Perry’s, 8:45pm).

Sunday 5
Undergrads rally around Little Dragon’s sleek electro-pop (Perry’s, 3:15pm) as Austin bluesman Gary Clark Jr. (PlayStation, 3:15pm) shows those who remember the Reagan era his best 12-bar salute, serving up some of the most heartfelt music heard on that stage since Blues Fest. From there, a calorie-burning trek south leads to the transcendent sounds of Sigur Rós (Red Bull Soundstage, 4pm). As hundreds of young’uns flock to Florence & The Machine (Bud Light, 6:15pm) for her sweeping pop epics, those Afghan Whigs fans from Friday are picking at leftover Aussie truffles (there’s a booth for that, too), huddled in anticipation of another dusted-off act, At the Drive-In (Red Bull Soundstage, 6pm). For the finale, they pound an espresso from La Colombe before staking out a spot for Jack White (Red Bull Soundstage, 8:15pm), as co-eds flit between the pop-culture-consumed rhymes of Childish Gambino (Google Play, 8:45pm) and Justice’s haute electro (Bud Light, 8:30pm). Fingers crossed we all go home dry this time.

Lollapalooza fills Grant Park Friday 3–Sunday 5. Visit out blog for extensive live coverage throughout the weekend.