Eminem & Rihanna - Lollapalooza 2014

Eminem headlined the opening night of Lollapalooza at Chicago's Grant Park on August 1, 2014, delivering one of the festival's most memorable performances. The biggest surprise came when Rihanna suddenly joined him onstage, turning an already huge headlining set into a preview of their upcoming Monster Tour.

Eminem was already one of the biggest names on the 2014 Lollapalooza lineup, and his performance covered an enormous amount of ground. The set moved through material from The Slim Shady LP, The Marshall Mathers LP, The Eminem Show, Recovery, and The Marshall Mathers LP 2. He also brought Royce da 5'9" out for “Fast Lane.”

The early portion of the show was essentially a greatest-hits sprint. “Square Dance,” “Business,” “Kill You,” “White America,” “Mosh,” “Rap God,” “The Way I Am,” and “Just Don't Give a Fuck” gave the Chicago crowd a reminder of just how deep Eminem's catalog had become.

Then came the moment everyone would remember. Rihanna appeared as a surprise guest for “Love the Way You Lie” and “The Monster,” two of the biggest collaborations of Eminem's career. She also joined him for “Stan,” taking the role associated with Dido in one of Eminem's most famous songs.

The timing couldn't have been better. Eminem and Rihanna were only days away from launching their joint Monster Tour, so the Lollapalooza appearance effectively became an unexpected warm-up for what would become one of the year's biggest concert tours. The surprise was significant enough that it became one of the defining stories of Lollapalooza's opening night.

After Rihanna left the stage, Eminem returned to his own catalog with “Sing for the Moment,” “Like Toy Soldiers,” “Forever,” “Berzerk,” “'Till I Collapse,” “My Name Is,” “The Real Slim Shady,” and “Without Me.” He closed the main set with “Not Afraid” before returning for “Lose Yourself.”

The complete performance ran an astonishing 31 songs when all of the abbreviated tracks and guest appearances are counted. It was a remarkably ambitious festival set, especially considering how many songs Eminem managed to represent in a relatively limited amount of time.

For the Lollapalooza crowd, though, the surprise appearance by Rihanna was the moment that elevated the night from a great Eminem show to something truly unforgettable. Seeing the two performers together just days before their joint tour began gave Chicago fans something that most festival audiences never get: a completely unexpected glimpse of a major musical partnership at exactly the moment it was reaching its peak.