Ashlee's Second Act

About to turn 21, Jessica's little sis is back in the spotlight with a new album, a new style and her own voice. By Serena Kappes with Carrie Borzillo-Vrenna

01 of 13

ME TIME

ME TIME
Jason Merritt/FilmMagic

"No matter what situation goes on, no matter what boy breaks my heart, I always remain who I am," says Ashlee Simpson of calling her sophomore album I Am Me (due in stores on Oct. 18).

02 of 13

MEET THE FANS

MEET THE FANS
Jason Merritt/FilmMagic

"I was doing it for fun," the actress turned singer (at the MTV Video Music Awards in August) says of recording her triple-platinum 2004 album Autobiography. "I never thought my CD would ever do as well as it has done." She hasn't left the screen behind: Simpson, who got her start on the WB show 7th Heaven, played a struggling actress in this summer's indie drama Undiscovered.

03 of 13

MISS METAMORPHOSIS

MISS METAMORPHOSIS
Kevin Mazur/WireImage; Bill Davila/startraks

Simpson is constantly experimenting with her look, evolving from funky (left, in 2004) to sophisticated (in Giambattista Valli at the VMAs). And she's gone back to being blonde: "I was really sick of getting my roots done – it looked like I was balding when they'd come in." She admired Gwen Stefani's platinum tresses so much that she even used the singer's colorist.

04 of 13

MORE THAN FRIENDS?

MORE THAN FRIENDS?
LDP Images

Since getting together in 2003, Simpson and singer Ryan Cabrera (onstage at the Orange Bowl in January) have had an on-and-off relationship. Even after reportedly breaking up last summer, they've shown up looking cuddly as recently as last month. When asked if they had rekindled their romance, Simpson simply said: "Me and Ryan? We're really good."

05 of 13

HOME SWEET HOME

HOME SWEET HOME
Celebrity Home Photos

One of her recent major purchases: a 9,000-sq.-ft. home on an acre of land in California's San Fernando Valley. "It's modern," says Simpson, who's staying with her parents until renovations are completed.

06 of 13

KISS AND MAKE UP

KISS AND MAKE UP
Kevin Mazur/WireImage

Lindsay Lohan reportedly turned Simpson and sister Jessica away from an L.A. party she hosted in June after Simpson supposedly shared a smooch with Lohan's ex, Wilmer Valderrama. But at the VMAs in August, all seemed to be forgiven. "Apparently the chill is over," says a source.

07 of 13

ROLE PLAY

ROLE PLAY
Michael Caulfield/WireImage

Simpson gives a tongue-in-cheek response to gossip that she had designs on Valderrama in the video for her single "Boyfriend." "The concept is that I stole somebody's boyfriend, but there's no real proof of it," she says of the clip, which she filmed while cruising in a vintage black Mustang in downtown Los Angeles on Sept. 1. "It was me and my mom's idea. We thought it would be funny."

08 of 13

GROWING UP

GROWING UP
London Entertainment/Splash

"I'm so excited!," says Simpson (with her pooch in West Hollywood in January) of turning 21 on Oct. 3. Where will she spend her big day? "Vegas … I'll be there gambling." And she'd like to celebrate with some bubbly. "I want so much wine and champagne. I have the wine rack. So I want to fill that up."

09 of 13

OOPS … NEVER AGAIN

OOPS NEVER AGAIN

After her lip-synching was revealed on the Oct. 23, 2004, episode of Saturday Night Live, "I didn't want to get out of my bed the next day," Simpson says. "The best part of it was overcoming it. Just saying, you know, that's life." She says the acid reflux that prompted her to use a backing track is now under control.

10 of 13

CLOTHES CALL

CLOTHES CALL
X17

A big fan of vintage tees, Simpson (shopping in Los Angeles last year) likes to buy "designer stuff, but I have to be comfortable." She's also handy with a knitting needle. "Knitting is so relaxing. Sometimes there are holes in my scarves, but they're supposed to be different," Simpson told Teen People recently. "They're authentic!"

11 of 13

REBEL, REBEL

REBEL, REBEL
Michael Caulfield/WireImage

Simpson (with stylist Ken Paves in L.A. on Sept. 1) "has a little punk edge to her," says her mom, Tina. The singer recently indulged her rocker side when, against her family's advice, she got two tattoos: cherries on her ankle and the word "love" on the inside of her left wrist. "I got 'love' because for me love is the most important thing," she says.

12 of 13

STAR OF THE SHOW

STAR OF THE SHOW
Theo Wargo/WireImage

"I do sing and write my own music," says Simpson (with her band in New York City last year). "That's something I hold really dear." She's looking forward to hitting the road this fall with a mini-tour to promote her new album.

13 of 13

FAMILY TIES

FAMILY TIES
Jamie McCarthy/WireImage

"Whenever we're in town, we make sure we have sister dates," says Simpson of older sibling Jessica (at a party in New York City in March). "The thing I learned from my family and my sister is that you have to look to them for support. At the end of the day, they're the ones that will have your back."

Related Articles