See All 8 of Drew Barrymore's InStyle Covers, from Her First in 1999 to Now

The actress was styled in Stella McCartney and Valentino for the November shoot, which took place at Pier 59 Studios in Manhattan. Between takes, she approved bindings for her new book of personal stories, Wildflower ($17; amazon.com), coordinated deliveries of her Flower Beauty line, and curated a playlist. 

The actress, then 38, graced the cover of our biggest issue ever (716 pages!) where we encouraged readers to “Do It Like Drew” and get her gorgeous look from our shoot with makeup products from her own beauty line, Flower.

We declared Barrymore "The Queen of Cool" and she lived up to that title. The 36-year-old actress talked about her then-boyfriend, now-husband, Will Kopelman and dished out sage aging advice: "I say, don't fight the rings on the trunk of the tree. Just keep counting 'em."

Barrymore made another appearance on our cover wearing a Valentino dress and Yves Saint Laurent jewelry while promoting her directorial debut, Whip It. For the photo shoot, we outfitted the 34-year-old in quirky fashions since she told us, "I love being the trippy one. I could never be conventional or prim."

On our September cover, Barrymore appeared wearing Armani to promote two new movies: Lucky You and Music and Lyrics. Then, like now, the 31-year-old displayed an enviable body confidence. "You learn to love your own body," she told us. "I'm not the kind of girl who can stuff her face with pasta all the time and not gain weight. I've been running and doing yoga and Pilates, and I love the way it makes my mind and body feel."

Eternal romantic Barrymore, then 28, appeared on our cover wearing an Emanuel Ungaro silk jersey dress. "Marriage is definitely not a goal right now, but I still want to have fun and be alive," she told us. "I am so in love with love." The star was promoting her 35th and 36th films, Confessions of a Dangerous Mind and Duplex.

A newly redheaded Barrymore, 25, was starring in the blockbuster hit Charlie’s Angels and thrilled with her hair makeover. "I find redheads so sexy," she said. "To play in their field is so much fun. Also, I'm a repressed hairdresser, so I love trying to get the right shade of red."

After 23 years acting, then 24-year-old Barrymore started a new career as a producer with her first feature film, Never Been Kissed. "The work was so much fun," she told us. "It takes up every second of your time and you never get upset for a second. In fact you're like, 'More, more—more hours in the day!"