Oprah at 2 years old

At 2 years old, Oprah says she's not the only one who had this hairstyle. "Every black woman of a certain age will notice this. Notice the bangs aren't really cut?" she says. "They're rolled and tucked because in our generation, my grandmother would say, 'Your hair is your crowning glory.' You were never allowed to cut your hair. So I wanted the bangs like the little white girls had. But you couldn't have the bangs, so they would roll up your hair and then pin it so you could have a pretend bang. So that's a pretend, fake bang. That's why I look so sad."
Oprah as a child

Oprah as a young child.
Oprah at 13

Oprah at age 13.
Oprah's graduation picture

"That's my graduation picture," Oprah says. "Press and comb."
Oprah at her first job in television

Oprah poses for a WLAC photo in Nashville. "That was my first job working in television," she says. "I could now afford a relaxer."
Oprah has a jheri curl.

Oprah says she had a jheri curl in this do. "But mild jheri curl. I always said mine wasn't greasy," she says.
Oprah's hair in Baltimore

An anchor in Baltimore at the time, Oprah says she settled on this hairstyle after a bad perm made her hair fall out.

Watch her tell the story. Watch
Oprah's audition tape

This hairstyle helped get Oprah hired when she auditioned to host a Chicago morning show.
Oprah's hair when she first arrived in Chicago

Circa 1986
Oprah says her longtime hairstylist, Andre Walker, was "experimenting" with her hair when she arrived in Chicago.
Oprah interviews Elizabeth Taylor

Looking back over 20 years, there's only one interview that Oprah calls her worst: Elizabeth Taylor. "It's still painful to watch," she says, "For many reasons—including my bad hair." 

Right before the interview, Liz asked Oprah not to ask her anything about her relationships. "That's kind of hard to do when you're Elizabeth Taylor and you've been married seven times," Oprah says. Liz's responses were so terse that Oprah couldn't help but tease, "You're so revealing—you just tell everything! I declare, you've got to stop talking so much, Ms. Taylor!"

"To her credit, she later apologized to me," Oprah says. One of the reasons why that interview seemed so painful is because Liz was in a lot of hip pain and back pain at the time.
Oprah's hair in 1994

Oprah wears her hair short.
Oprah's hair in 1997

Oprah keeps her hair short with bangs.
Oprah's hair in 1999

Oprah wears a longer, straight style.
Oprah's hair in 2002

Oprah wears her hair short once again.
Oprah's hair in 2003

Oprah's hair is longer and flipped up on the ends.
Oprah's hair in 2004

Oprah's hair is shoulder-length and straight.
Oprah's hair in 2005

Oprah channels her inner Tina Turner during the singer's appearance on the show. "I wanted to look like Tina wearing a wig," she says.
Oprah's hair in 2005

Oprah wears a curly 'do.
Oprah's hair on the road trip

Oprah wore braids during her cross-country road trip with Gayle.
Oprah's hair in 2006

Oprah wears her hair in a ponytail.
Oprah's hair in 2007

Oprah pulls her hair back in a curly look.
Oprah and Chris Rock

During a taping with Chris Rock, Oprah wears her real hair. She credits Andre for helping her keep her real hair for 24 years. "In the summer, I braid my hair. I wear weaves. I've worn weaves on the show. I've worn weaves on the magazine covers," she says. "I have done pretty much all of it because in order to keep your hair, you can't put heat in your hair every day."

Watch Chris Rock's reaction when he finds out Oprah's hair is real. Watch

Oprah Winfrey's hair for finale show

Oprah and her hairstylist, Andre Walker, were wishing they had more time for this style to set before The Oprah Winfrey Show finale taping. We think it turned out to be the perfect look for Oprah to bid farewell.
Watch Oprah take her show stage for the last time.
Oprah's natural hair

Oprah appeared on the cover of O's September 2012 issue with an au naturel 'do that required no blow-drying or straightening. She says that wearing natural styles makes her feel unencumbered.
Oprah Winfrey at the 6th Annual Essence Black Women in Hollywood Luncheon


This style, which Oprah wore to the 6th Annual Essence Black Women in Hollywood event, reminds us of one of her favorite music icons, Diana Ross.