NEW YORK, NY.- Irving Penn's Harlequin Dress, Lisa Fonssagrives-Penn, 1950, a Platinum-Palladium print from 1979, an acknowledged masterpiece from one of the greatest fashion photographers to ever pick up a camera, is expected to bring $150,000+ to lead Heritage Auctions' May 2 Signature Vintage & Contemporary Photography Auction, taking place at the Fletcher-Sinclair Mansion, 2 East 79th Street.

This legendary image is accompanied by four more Penn images in the auction, including Penn's Woman in Dior Hat with Martini (Lisa Fonssagrives-Penn), 1952, a Gelatin Silver print, estimated at $30,000+.

"The five Penn photographs in this auction underscore the overall quality that we've assembled for this auction," said Ed Jaster, Senior Vice President of Heritage Auctions. "Without a doubt this is our deepest Photography auction yet and I believe that collectors have noticed and will respond accordingly to the quality of the material."

Half a dozen photographs from early 20th Century master photographer Edward Weston infuse the auction, including a vintage gelatin silver print of Weston's Pepper (No. 14), 1929 (estimate: $50,000+) and his elegant and understated Nude, 1936 (estimate: $5,000+), a gelatin silver printed later by Weston's son, Cole. Continuing the great American photography from the top names of the early 20th Century, Heritage will be offering 12 images from the lens of America's greatest naturalist photographer, Ansel Adams, led by his impressive Moon and Half Dome, 1960, a gelatin silver print from c. 1970, estimated at $25,000+.

Few modern American photographers are more influential, collectible and highly revered than Annie Leibovitz, and the May 2 Heritage event will not disappoint collectors with five examples of Leibovitz's work making an appearance in the auction, led by a print of what is likely her most famous photo, John and Yoko, New York, December 8, 1980, estimated at $20,000+.

"This famous image was taken on the morning of Dec. 8, 1980 at The Dakota, tragically the same day Lennon was shot," said Jaster. "Beyond being Leibovitz's most famous image, it's easily the most recognizable, and likely the greatest, rock and roll magazine cover image ever, appearing as it did as the cover to the January 1981 Rolling Stone issue dedicated to Lennon. Few images have ever so clearly conveyed both its subject and its meaning to broader public than this iconic photo."

Helmut Newton was one of the great fashion photographers of all time and his work continues to be in demand at auction, as evidenced by the four examples in this auction, including a vintage gelatin silver print of his Roselyne at Arcangues, 1975, estimated at $35,000+, while the work of Robert Mapplethorpe, a photographer whose work has continued to climb in both price and estimation since his death more than two decades ago, is well-represented with his Urn with Fruit, 1987, expected to bring $20,000+.

Rounding out the Contemporary offerings are Massimo Vitali's Calafuria #1774, 2002, a Chromogenic print expected to bring $10,000+, while David Drebin's Hotlanta, 2005 is expected to be the subject of spirited bidding, with an estimate of $7,000+.