Take me back to Summerfest 1999: Brandy at Marcus Amphitheater

When you look at Summerfest lineups from year to year, certain patterns start to emerge. Due to the impossible task of trying to please everyone, as well as behind the scenes factors like budget, tour routing, and the rampant competition brought on by countless other festivals that have spouted up since Summerfest’s inception more than 50 years ago, sometimes “The World’s Largest Music Festival” plays it safe when it comes to choosing headliners.

It’s easier to book an act that’s between album cycles, get in touch with the management of a previous Big Gig performer, and run it back with someone familiar instead of incurring the risk of trying to latch onto a rapidly rising star. That’s not to say Summerfest doesn’t also take big swings in addition to reprising almost perennial crowd-pleasing headliners like Def Leppard, The Avett Brothers, and George Thorogood & The Destroyers.

The list of “years before they were world famous” free stage bookings could fill multiple books. The legends the festival has coaxed back to Milwaukee to play a one-off show is astounding. The just-before-breakout foresight Big Gig bookers have displayed on occasion is also impressive. And sometimes, the very same festival where you can gain entry to see O.A.R. or Third Eye Blind by donating three non-perishable goods will also bring an artist to town at the absolute peak of their popularity. As we wait to see whether July 3 AmFam headliner Benson Boone winds up in that last category, let’s look into an undeniable case of Summerfest landing a colossal artist at the exact perfect point in their career.

On June 9, 1998, Brandy Norwood—better-known across the universe as just “Brandy”—released Never Say Never. The 19-year-old singer’s sophomore album soared up the charts that summer after the release of lead single, “The Boy Is Mine” (an adversarial duet with fellow single-name R&B talent Monica). Another five acclaimed singles would follow in subsequent months, which would keep the breakout record in radio and MTV rotation en route to selling 16 million copies, going Platinum five times, and finding Never Say Never peaking at Billboard‘s number two album.

Simultaneous to her success in the realm of music, Brandy was also making waves as an actor. She starred opposite Whitney Houston in the title role in a 1997 TV movie version of Cinderella and had a prominent part in 1998 slasher sequel I Still Know What You Did Last Summer. Of course, she was also the lead of the classic UPN sitcom Moesha, which had just wrapped its fourth season by the time Brandy was finally able to embark on a world tour in belated support of her certified hit album. In fact, her acting career had a great deal to do with the “Never Say Never World Tour” being pushed to the summer of 1999.

In May 1999 (three months after winning a Grammy for “The Boy Is Mine”), Brandy took the stage in Paris to kick off her well-deserved and long-overdue world tour. Another eight European concerts followed, then four in Japan before she returned stateside for the U.S. leg that was supposed to extend into early August. Ultimately, Brandy was forced to cancel the last 20 shows of the “Never Say Never World Tour” so she could start shooting season five of Moesha.

However, one of the mere 12 concerts Brandy performed in the country (and the only festival stop) as part of the abbreviated world tour happened at Marcus Amphitheater on July 1, 1999 during Summerfest. And despite being a devoted Moesha viewer and an unabashed fan of Brandy’s music, I wasn’t there. Since it was more than a quarter-century ago and I wasn’t in attendance, I unfortunately cannot give you an exact rundown of the July 1 show itself. Yet based on what I know about the tour itself, it sounds like Brandy’s Milwaukee debut had the makings of being a Summerfest all-timer.

Opening duties on the tour were split between C-Note, pre-Fast & Furious Tyrese, and 702 of “Where My Girls At” fame. No matter which combination of them Brandy brought with her to Milwaukee, the amphitheater was in for a good aural appetizer. Even though I can’t find a set list for this specific concert, I imagine it closely mirrors—or is likely an exact replica of—the set list for the rest of the tour, which is not-so-coincidentally also the set list for her UPN concert special that she would film six days after the Milwaukee performance (more on that later). Obviously gearing up for filming, it had to be the same set list, right?

Assuming that was the case, that meant Brandy chased an introductory overture with Never Say Never deep cut/undebatably lively show-starter “Happy” to get the amphitheater’s energy up from the jump. Tone set, “Baby” and “I Wanna Be Down”—both high points from the young phenom’s star-making 1994 self-titled debut album—came next, followed by another Brandy track, a ballad called “Brokenhearted,” that offered attendees a break from dancing and did service to the “early” material or a prodigy who was a few months removed from turning 20.

During the four-year span between albums one and two, Brandy contributed a song to the soundtrack for the 1995 film Waiting To Exhale. That song, “Sittin’ Up In My Room,” was produced by Kenneth “Babyface” Edmonds and it somehow manages to outshine other soundtrack offerings from the likes of Whitney Houston, Toni Braxton, Aretha Franklin, Mary J. Blige, Patti LaBelle, and Faith Evans. So of course she was going to perform it on her first world tour as a mid-set boost and a beloved song to bridge her two albums!

The latter half of the set leaned heavily on Never Say Never, and rightfully so. Had my 14-year-old self been there, I would’ve thrown a mid-puberty conniption fit if Brandy came to my state and deprived Wisconsin of hearing “Almost Doesn’t Count” and “Top Of The World” (even if Ma$e wasn’t actually there to perform the latter with her). You better believe she also captivated the crowd with “Have You Ever” and—the biggest song of 1998 and her entire career—”The Boy Is Mine” during her on-stage traversing of her year-old album she was finally traveling (part of) the world to honor.

As I already mentioned, I wasn’t there, but I feel comfortable guessing how it went because on July 7, 1999, Brandy canceled the “Never Say Never World Tour” with 20 stops left, and filmed a performance at Rosemont Theatre in Rosemont, Illinois that would air on UPN in December 1999 as Brandy In Concert: A Special For The Holidays. In the clips I’ve seen, Brandy sounds incredible, she looks stunning (even when factoring the era-specific wardrobe), her choreography is on point, and her live band is killing it. If Marcus Amphitheater got to witness a spectacle that was even half as good as the audience at the special taping saw six days later, it would’ve been a show for the ages.

Miraculously, Brandy has only returned to Milwaukee one other time to perform. She came to town June 13, 2009 to headline PrideFest as part of her “Human World Tour.” I was mere months away from moving to Milwaukee at that point, and I missed that show as well. Earlier this week, Brandy and Monica announced their co-headlining “The Boy Is Mine Tour” that includes a stop at Fiserv Forum on Friday, October 17. I’m going to start saving up now so I don’t make the mistake of missing Brandy a third time.

As much as I know this fall’s show is going to rule, I truly wish I could go back to July 1, 1999 to experience the night Summerfest caught lightning in a bottle and hosted an absolute superstar at her peak for one of just 25 shows in support of a truly iconic R&B album. Take me back to that time Milwaukee was sitting on top of the world with Brandy headlining the Marcus Amphitheater.