It's hard to believe, but five years have passed since the release of Kevin Federline's debut Playing With Fire, which came out on Halloween, 2006. It was a scary night for some, but K-Fed was on top of the world. Married to Britney Spears, he was psyched to finally bring his brand of hip-hop to the world.

Only six days later, however, he suddenly found his life in the gutter. The catalyst? His first live concert ever, held at New York's Webster Hall. It was a complete and utter disaster.

Kevin Federline is not a fan of the paparazzi, or as he calls them, the "Pavarottis"; Credit: Christiana Cefalu

Kevin Federline is not a fan of the paparazzi, or as he calls them, the “Pavarottis”; Credit: Christiana Cefalu

But before we bring you this chilling tale, a quick timeline of preceding events to get you up to speed:

9/27/04: After five blissful months of courtship, Federline and Spears get married in a “pimps and hoes” themed ceremony in Studio City.

5/17/05: Federline and Britney's self-produced reality show Britney & Kevin: Chaotic debuts on UPN. It is not renewed for a second season.

9/14/05: Their son Sean Preston is born.

11/2/05: A snippet of “Y'all Ain't Ready,” the first time we get to hear Federline rap, is leaked by producer Disco D. It is greeted by a tidal wave of hatred.

1/1/06: Federline officially releases his first single “Popozao,” accompanied by a video of him playing it in the studio. The video becomes an internet meme.

4/5/06: Thomas Dolby attempts to take legal action against Federline for sampling his song “She Blinded Me With Science.” His case stalls because, according to Dolby, Federline has no management, label or lawyer.

8/20/06: Federline makes his live performance debut at the 2006 Teen Choice Awards.

10/16/06: He appears on WWE Monday Night Raw to promote his upcoming album. The crowd's disdain for him convinces management to have him return the next week as a villain, and he begins a three month feud with fan favorite John Cena.

10/31/06: Playing with Fire is released on Federation Records, Federline's imprint on the short-lived Reincarnate Music label. Moving 6,485 copies, it charts at 151 on Billboard, which doesn't sound too hot, although it outsells new releases from Flava Flav, Ice-T, and Ron Artest and greatest hits albums from Cee-Lo and Lil Romeo. Still, it remains the lowest-scoring work ever in Metacritic's database.

The worst night of K-Fed's life begins below.

K-Fed's Webster Hall merch booth sold t-shirts, CDs and dreams; Credit: Christiana Cefalu

K-Fed's Webster Hall merch booth sold t-shirts, CDs and dreams; Credit: Christiana Cefalu

On November 6th, 2006, the stage was set for Federline to finally prove the haters wrong. That evening in Manhattan he stepped into his destiny. Well, he stepped in something anyway. (Attempts to reach Federline for this story were unsuccessful.)

“We walked into Webster Hall and there was nobody there,” remembers Christiana Cefalu, an NYU freshman at the time. She purchased tickets weeks in advance with a group of her classmates, hoping for a memorably absurd night. (To their dismay, free tickets were being given away at the door.) To pass the time before the show started, they bought some t-shirts and took pictures with folks manning the merch booth, above.

There was no opening act. After several hours of waiting Federline finally came on, and proceeded to scowl through eight songs. On the stage with him were two back-up dancers, a DJ, and bottles of Jack Daniels and Pepsi.

Federline seemed to be angry; between songs he yelled “Fuck the media.” Eventually, a small crowd amassed — about four rows deep — and they were fairly respectful. Many in the NYU group, however, were disappointed that he did not play “Popozao.” That didn't stop Cefalu from snagging the set list, however, which was written on a paper plate and which you can see below, typos and all.

You win some you loose some; Credit: Christiana Cefalu

You win some you loose some; Credit: Christiana Cefalu

By all accounts the performance was less than compelling. But, hey, anyone can have a bad night — especially if it's your first show. Unfortunately the next morning things got worse, when Federline discovered via text message that Britney was leaving him.

Twenty-four hours later, during a performance at Chicago's House of Blues, Federline addressed the crowd: “You know I'm a free man? You want to dance with a pimp?”

Subsequent shows in Cleveland and Atlantic City were cancelled due to poor ticket sales. Spears had a mental breakdown, and Federline's rap career was put on the back burner during their impending divorce.

While he did return to the mic for a hilarious Super Bowl commercial and an unreleased song with Bone Thugs-n-Harmony three years later, K-Fed's top priority as of late has been his new baby girl with girlfriend Victoria Prince.

Life came at K-Fed fast. Though his rap career will likely remain a punchline, perhaps it is better to have VIPed and lost than to never have VIPed at all.

LA Weekly