In what was a controversy-free evening, the rapper and boyfriend of Beyonce scored big for "99 Problems," his gritty black-and-white clip that ends with him getting gunned down. But video of the year honors went to the night's other four-time winner, OutKast, for "Hey Ya!" – which also won best hip-hop video, best special effects and best art direction.
Upon picking up his trophy for best rap video, Jay-Z noted: "I feel like I was pushing the envelope to punish you, and this is my reward." (The video also scored for best direction, best editing and best cinematography.)
Both he and Beyonce said "what up" to each other during their speeches – she upon winning best female video for "Naughty Girl," topping Britney Spears, Alicia Keys, Jessica Simpson and Christina Aguilera.
Besides OutKast and Jay-Z, the evening's other big winner was the chiseled chested Usher, who got the show's musical performances rolling with a medley featuring Lil' Jon and Ludacris. Up for five awards and the winner of two, Usher's "Yeah!" was named best male video and best dance video.
Winning the dance video prize, Usher rhetorically asked the crowd, "There's no more competition between me and Justin (Timberlake), right?"
Best pop video went to No Doubt for their cover of "It's My Life," while Alicia Keys scored best R&B video for "If I Ain't Got You." Keys also put on one of the most memorable performances of the night, leading an all-star jam with Stevie Wonder and Lenny Kravitz for Wonder's classic "Higher Ground."
The viewer's choice award, which was promoted throughout the program by The Daily Show's Jon Stewart, went to Linkin Park, for "Breaking The Habit."
After stars arrived on the red carpet by boat rather than limo, Jennifer Lopez opened the show inside the AmericanAirlines Arena, and among those cheering her on was her husband, Marc Anthony, sitting ringside.
This year marked the first time that the show was based in the Florida hot spot rather than Los Angeles or New York – which, as of Sunday, was serving as home to the Republican National Convention.
Not that politics didn't have a presence at the VMAs. Carson Daly introduced first daughters Jenna and Barbara Bush (in New York) and John Kerry's daughters, Vanessa and Alexandra Kerry (onstage in Miami), who all talked up the importance of voting in November and to ask for help for those affected by the recent Hurricane Charley. A mixed reception greeted both sets of daughters.
Other notable performances Sunday were delivered by Kanye West with Chaka Khan, and Jessica Simpson. Aside from her show-stopping performance, Keys also helped conduct a tribute to the late Ray Charles.
Mary-Kate and Ashley Olsen also made their first public appearance since Mary-Kate entered treatment for an eating disorder. Holding her twin sister's hand, a poised Mary-Kate told the crowd: "First, I want to say thank you to everyone who has been very supportive of me the past several months."
Will Smith delivered a flashy introduction of Shaquille O'Neal, now with the Miami Heat, in what could only be described as a Shaq Attack – with the 7'1" former Laker stepping onto the stage floor, towering over people twirling strips of white fabric in time to the music.
Funnyman Dave Chappelle also appeared throughout the show, calling MTV's decision to allow him on the air "the biggest mistake since Janet Jackson went on the Super Bowl."
Arriving together: Bruce Willis (sporting a shaved head), Sean "P. Diddy" Combs (sporting a Mohawk) and Naomi Campbell, sporting a short, white toga. Combs hosted a bash at his Miami mansion Saturday night for 50 select guests, including Willis, Hilary Duff and Busta Rhymes.