2006

Kevin Federline

August 20

Rapping K-Fed

Federline performs his single "Lose Control" from his upcoming debut album Playing with Fire at the end of the Teen Choice Awards. "I'm happy," says Federline. "I think I pulled it off pretty well." But a EW reviewer disagrees, saying Federline "just strikes me as either completely clueless or just incredibly tenacious. And possibly deluded" because "I haven't heard of any sort of appearance that he's made where he hasn't been heckled and booed."

October

Marital Strife?

The once frequently photographed twosome now rarely appear in public together. Spears heads to Las Vegas to work on a new album while Federline gigs in L.A. alone. When they are both in New York, Spears doesn't attend Federline's album release party or concert.

Kevin Federline

October 12

Keepin' it Gangsta on CSI

Eager to prove that he is more than just Mr. Britney Spears, Federline ventures into acting as a street tough teen on CSI: Crime Scene Investigation. As cops haul him to jail on the hit TV drama, Federline yells, "Free shower, free food, free sleep…this little piggy went wee, wee, wee, all the way home!"

Kevin Federline

October 31

Federline's Fire

Federline releases his debut album Playing With Fire. "I'm the first white boy bringing the West Coast sound," he tells GQ. "It's gonna be huge. I'm doing s--- not even Eminem does." Rolling Stone gives the album one star, dubbing it a "tragicomedy" whose "rhyme flow is the opposite of tight." Even his promotional tour, which included getting body slammed (and booed) at WWE Monday Night RAW, can't combat the bad reviews; it sells 6,500 copies in its first week of release, entering the charts at No. 151.

Kevin Federline

November 07

From K-Fed to Fed-Ex

After months of being photographed in messy ponytails and questionable outfits, Spears looks amazingly stylish in a short black dress and blonde bob at David Letterman's Late Show. Right after the appearance, she files for divorce from Federline, citing "irreconcilable differences." Both parents ask for sole custody of their two boys. While Federline continues on his promotional tour, Spears parties in L.A. and Las Vegas with temporary BFF Paris Hilton.

2007

Kevin Federline

February 04

A New Career?

Federline plays a daydreaming fast food worker in a Nationwide Insurance commercial that debuts during the Super Bowl. Critics say the ad demeans fast-food workers. Taco Bell president Greg Creed reaches out to Federline in an open letter: "So here's our offer to you: Come work for us, just for a one hour shift. We'll get you a uniform, a custom name tag and show you what a great place Taco Bell is to work."

February 20

Stepping Up When Brit Is Down

Spears spirals out of control. Her excessive parting and bizarre behavior ends with a stint in rehab. Federline steps in to take care of their two boys, and sources tell PEOPLE that he played a role in persuading Spears to enter rehab in the first place. Federline works closely with Spears' mom Lynne to help his estranged wife and brings their sons to visit her at rehab. On March 20, Spears is released from Promises.

Kevin Federline

August

Battling Britney for Custody

After their divorce is finalized, Federline files for primary physical custody of their two boys and subpoenas Spears' friend Alli Sims, her bodyguard Daimon Shippen and former assistant Shannon Funk. In September, a judge rules Spears must undergo random drug testing, meet with a "parenting coach," and with Federline complete a program called "Parenting Without Conflict." A few weeks later, Federline wins temporary custody of the boys.

Kevin Federline

December

Influential as 'Good Father'

Federline is named one of Details' 50 Most Influential Men Under 45. The 29-year-old father of four shares the 7th spot with Anna Nicole Smith's ex Larry Birkhead – under the title "The Good Fathers." Details declares, "By being more visible presences in their children's lives than many Hollywood A-listers, they emerged as unlikely candidates for Dad of Year."

2008

Kevin Federline

Custody Crisis

In early January, Federline is transferred custody of his children with Spears after she breaks under pressure and ends up in the hospital under mental lockdown. In July, after a year-and-a-half court battle over their two sons, Federline and Spears reach a custody settlement, with Federline retaining sole custody. Spears is granted visitation rights.

Photo Credits

BIOGRAPHY (top to bottom): Debbie VanStory/IPHOTO; Robert Voets/CBS; amazon.com; INF;Jamie McCarthy/WireImage; Splash News Online

Edited by Mai Dinh, Janet Murphy