Smith appeared on the cover of the March 1992 issue of Playboy magazine, with her name given as Vickie Smith. She later appeared as the Playboy Playmate of the Month in a pictorial shot by Stephen Wayda for the May 1992 issue.  Smith then secured a contract to replace supermodel Claudia Schiffer in a Guess jeans ad campaign featuring a series of sultry black-and-white photographs. During the Guess campaign Smith changed her name to Anna Nicole Smith. Guess photographers noticed Smith bore a striking resemblance to bombshell Jayne Mansfield and showcased her in several Mansfield-inspired photo sessions. In 1993 before Christmas, she modeled for the Swedish clothing company H&M. This led to her being pictured on large billboards in Sweden and Norway. In addition to Playboy, Smith appeared on the cover of German Marie Claire magazine, photographed by Peter Lindbergh  A photograph of Smith was used by New York magazine on the cover of its August 22, 1994, issue titled White Trash Nation. In the photo, she appears squatting in a short skirt with cowboy boots as she eats chips. In October 1994, her lawyer, T. Patrick Freydl, initiated a $5 million lawsuit against the magazine, claiming that Smith did not authorize the use of her photo; the suit also alleged that the article damaged her reputation. Her lawyer stated Smith was under the impression that she was being photographed to embody the "all-American look." Editor Kurt Andersen said that the photo was one of dozens taken for the cover, further stating "I guess they just found the picture we chose unflattering." The lawsuit was reported to be settled.

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