AI Appraisal Estimate

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Submitted photo · June 26, 2026

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AI appraisal

AI analysis & estimate

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Everything below is generated by AI for informational purposes only. AI can make mistakes — the AI may misidentify items or misattribute them (artist, maker, brand, designer, origin, era). This is not an official valuation and should not be used for insurance, sale, tax, estate, legal, or lending purposes — or any decision requiring a certified appraisal. It is not an authoritative claim about any person, brand, or rights holder — do not share or rely on it as a factual statement about a third party. Always consult qualified professionals before making financial decisions.

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AI Identification

·Not independently authenticated·Verify before acting

Playboy Magazine May 1999 Issue Featuring Charlize Theron

Collectibles / Magazines

AI Estimated Value

·Not an official valuation·Verify before acting

$10 - $25

As of June 26, 2026

AI Item Analysis

·AI can make mistakes·Verify before acting
This is a physical copy of the May 1999 edition of Playboy magazine, a notable publication in the adult entertainment industry. The cover prominently features actress Charlize Theron. The magazine is a standard-sized periodical with a glossy paper cover. The masthead 'PLAYBOY' is printed in gold-colored font, accompanied by headlines for featured articles including interviews with David Spade and Ashley Judd. The cover art is a close-up, high-glamour photograph typical of the era's aesthetic. Small white text in the top right corner indicates the price of $4.95 at the time of publication. The condition of the magazine appears relatively well-preserved, with sharp corners and vibrant colors, though a blister pack of four small button-cell batteries is placed over the lower center of the cover, partially obscuring the image. There is no major visible creasing or water damage from the perspective shown. As a late 20th-century collectible, its value is derived from the popularity of the cover model and the overall condition of the internal pages and centerfold. This specific issue represents a transition period in print media prior to the digital age.

AI Appraisal Report

·AI can make mistakes·Verify before acting
Based on my visual examination of this May 1999 issue of Playboy, featuring Charlize Theron on the cover, I would grade this item in Very Good to Fine condition. The cover colors remain vibrant, and the spine appears intact without significant rolling, which is crucial for collectors. The corners look sharp with minimal blunting. However, my assessment is slightly hindered by the obstruction of the button-cell battery pack placed on top of the cover in the image, which obscures potential surface scratches or indentations underneath. This specific issue is desirable primarily due to the cover model, Charlize Theron, who remains an A-list celebrity. Historically, Playboy issues from the late 90s were printed in high volumes, meaning scarcity is not a primary driver of value; condition is paramount. While the $4.95 cover price is noted, current resale values fluctuate based on the completeness of the issue (presence of all inserts and the centerfold). Market comparables for raw (ungraded) copies of this issue generally sell between $10 and $25 on platforms like eBay, depending on whether the centerfold is pristine. Graded copies (CGC) can fetch higher prices, but this copy is raw. Limitations of this appraisal include the inability to inspect the interior pages for potential moisture damage, missing coupons, or tears, and the inability to check the centerfold's attachment. A full physical inspection would be required to confirm the internal integrity and to ensure no hidden surface damage exists beneath the battery pack currently resting on the item.

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