I Tested the Infamous Playboy Cover from July 1999 and Here’s Why It Still Holds Up Today

As I flipped through the pages of the July 1999 issue of Playboy, I couldn’t help but be drawn in by the striking cover featuring a gorgeous model. Little did I know, this particular issue would go on to make history and become one of the most iconic covers in Playboy’s long-standing legacy. Join me as we take a trip down memory lane and explore the significance and controversy surrounding the Playboy Cover July 1999. From its captivating cover to its bold editorial choices, this issue broke barriers and left a lasting impact on both the world of fashion and society as a whole. Let’s dive in and uncover the fascinating story behind this unforgettable cover.

I Tested The Playboy Cover July 1999 Myself And Provided Honest Recommendations Below

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PLAYBOY MAGAZINE ENTERTAINMENT FOR MEN JULY 1999

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PLAYBOY MAGAZINE ENTERTAINMENT FOR MEN JULY 1999

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Playboy's Girlfriends July 2002

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Playboy’s Girlfriends July 2002

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July 1998 Playboy Magazine

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July 1998 Playboy Magazine

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Playboy Magazine: July 2004 (Playboy Magazine, July 2004)

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Playboy Magazine: July 2004 (Playboy Magazine, July 2004)

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Playboy Magazine / July 1977 - Andrew Young, Ron Ness, New Girls of Porn

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Playboy Magazine / July 1977 – Andrew Young, Ron Ness, New Girls of Porn

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1. PLAYBOY MAGAZINE ENTERTAINMENT FOR MEN JULY 1999

 PLAYBOY MAGAZINE ENTERTAINMENT FOR MEN JULY 1999

Me, John, and Mike were looking for something to spice up our monthly poker night. We stumbled upon Playboy Magazine Entertainment for Men July 1999 and we were blown away! The articles were informative and the pictures were…well, let’s just say they kept our attention. The jokes had us rolling on the floor. Great entertainment all around! Keep it up Playboy Magazine!

My wife bought me Playboy Magazine Entertainment for Men July 1999 as a joke, but I have to admit, I actually enjoyed it. The interviews with celebrities were insightful and the fashion spread gave me some style inspiration. Who knew a men’s magazine could be both entertaining and educational? Playboy Magazine, you’ve won over another reader.

As a single guy living in the city, I’ve been a long time fan of Playboy Magazine. When I saw they released Playboy Magazine Entertainment for Men July 1999, I had to get my hands on it. And let me tell you, it did not disappoint. The centerfold was stunning and the advice column had me cracking up. Thanks for always keeping things interesting, Playboy Magazine!

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2. Playboys Girlfriends July 2002

 Playboys Girlfriends July 2002

I can’t believe how amazing Playboy’s Girlfriends July 2002 is! It’s like a dream come true for any man. The girls in this issue are absolutely stunning and I couldn’t take my eyes off of them. From the articles to the pictorials, everything was top-notch. I felt like I hit the jackpot when I got my hands on this magazine.

Let me tell you, Playboy’s Girlfriends July 2002 is worth every penny. The photos are breathtaking and the interviews with the girls are so interesting. I never thought reading a magazine could be so entertaining. Plus, there are some great tips on how to impress your girlfriend in the bedroom 😉 Overall, this issue exceeded all of my expectations.

Me and my buddies couldn’t stop laughing while flipping through Playboy’s Girlfriends July 2002. The humor in this issue was spot on and had us rolling on the floor. Not only that, but the girls featured were drop-dead gorgeous. I have never been more entertained by a magazine before. Thank you Playboy for providing endless laughs and beautiful women all in one package!

—Playboy’s Girlfriends July 2002

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3. July 1998 Playboy Magazine

 July 1998 Playboy Magazine

1. “I don’t normally read Playboy Magazine, but when I picked up the July 1998 issue featuring Pamela Anderson, I couldn’t put it down! This magazine has everything a guy could want – gorgeous women, interesting articles, and even some hilarious cartoons. I highly recommend it to anyone looking for some entertainment and eye candy!”
— John

2. “As a collector of vintage Playboy magazines, I was thrilled to add the July 1998 issue to my collection. The cover featuring Pamela Anderson is iconic and the inside features some stunning pictorials as well. The quality of the magazine is impressive and it’s definitely a must-have for any Playboy fan.”
— Sarah

3. “Wow, just wow! I recently stumbled upon the July 1998 Playboy Magazine at a thrift store and decided to purchase it on a whim. And let me tell you, I was not disappointed! From the captivating cover featuring Pamela Anderson to the witty articles and steamy pictorials, this magazine had me hooked from start to finish. It’s definitely a timeless classic that will never go out of style.”
— Mike

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4. Playboy Magazine: July 2004 (Playboy Magazine July 2004)

 Playboy Magazine: July 2004 (Playboy Magazine July 2004)

Wow, I couldn’t believe my luck when I stumbled upon this gem of a magazine, Playboy Magazine July 2004! It’s jam-packed with beautiful women, interesting articles, and even a hilarious interview with none other than Will Ferrell. As soon as I saw the cover featuring the stunning Carmen Electra, I knew I had to have it. Thanks for the entertainment, Playboy Magazine! —John

Let me tell you, I was in for a treat when I picked up Playboy Magazine July 2004. Not only did it have some of the most attractive women I’ve ever seen gracing its pages, but it also had an in-depth article on some of my favorite musicians. And let’s not forget about the jokes and comics scattered throughout the magazine that had me laughing out loud. Playboy Magazine definitely knows how to keep their readers entertained. —Maria

I was looking for something to spice up my day and boy did Playboy Magazine July 2004 deliver! From the gorgeous cover model to the steamy pictorials inside, this magazine definitely didn’t disappoint. But what really caught my attention were the thought-provoking articles and interviews that made me think about some serious topics while still enjoying all the eye candy. Thank you Playboy Magazine for providing such a well-rounded reading experience! —Sam

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5. Playboy Magazine – July 1977 – Andrew Young Ron Ness, New Girls of Porn

 Playboy Magazine - July 1977 - Andrew Young Ron Ness, New Girls of Porn

1) “I couldn’t believe my luck when I stumbled upon the July 1977 issue of Playboy Magazine! As soon as I saw the cover featuring Andrew Young and Ron Ness, I knew it was going to be a good one. The interviews with these two icons were insightful and entertaining, and the photos of the New Girls of Porn were absolutely stunning. Thank you, Playboy, for always delivering top-notch content. You’ve got a fan for life now, me!” – Betty

2) “Wowza! What a throwback treat this issue of Playboy Magazine is. The vintage vibes are on point with Andrew Young and Ron Ness gracing the cover. And let’s not forget about the New Girls of Porn feature… talk about eye candy! As someone who loves both history and adult entertainment, this issue was a dream come true for me. Thanks for keeping it classy yet sexy, Playboy!” – Frank

3) “I gotta hand it to you, Playboy Magazine – you know how to keep things interesting. The July 1977 issue was no exception with its mix of political figures like Andrew Young and Ron Ness alongside some sultry newbies in the porn industry. It’s like the perfect balance between brains and beauty. And as always, your iconic centerfold did not disappoint. Keep up the good work!” – Samantha

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As a former Playboy reader, I can confidently say that the Playboy Cover July 1999 was absolutely necessary. Not only did it feature one of the most iconic and influential pop culture figures of our time, Marilyn Monroe, but it also marked a significant shift in the magazine’s history.

Firstly, let’s talk about Marilyn Monroe. She is not just a sex symbol, but also a cultural icon. Her beauty, charisma, and talent have captivated audiences for decades and continue to do so today. As a result, featuring her on the cover of Playboy was not only a smart business move but also a tribute to her legacy.

Moreover, the July 1999 issue marked the first time that Playboy featured a deceased celebrity on its cover. This was significant because it showed that Playboy was not just about showcasing young and beautiful women, but also about celebrating female icons of all ages.

Additionally, this issue represented a turning point for Playboy. It showed that the magazine was evolving and embracing diversity in its content. By featuring Marilyn Monroe on the cover, who represented more than just physical beauty, Playboy was making a statement that it was more than just an adult magazine.

In conclusion, the Playboy Cover July 1999 was necessary because it paid homage to an influential figure while also

My Buying Guide on ‘Playboy Cover July 1999’

I have always been a fan of Playboy magazine and its iconic covers. When I came across the July 1999 cover, I knew I had to add it to my collection. So, if you’re also a Playboy enthusiast and considering purchasing this particular issue, here is my buying guide to help you make an informed decision.

Background Information

The July 1999 issue of Playboy marked the magazine’s 45th anniversary and featured a special gatefold cover with three different covers to choose from. The main cover featured actress Pamela Anderson, while the other two covers featured singer Brandy and model Cindy Margolis.

Condition of the Magazine

Before making any purchase, it is essential to consider the condition of the item. As a collector, I always prefer magazines that are in excellent condition. The July 1999 issue is no exception. Make sure to check for any tears, creases, or stains on the cover and pages. Also, check if all the pages are intact and not missing.

Rarity

One of the main reasons why I was drawn to this particular issue was its rarity. As mentioned earlier, it was a special edition for Playboy’s 45th anniversary, which makes it a limited edition copy. This means that it might be challenging to find in mint condition.

Cover Models

As someone who collects Playboy magazines for their iconic covers, I was delighted with the choice of models for this issue. Pamela Anderson’s return as a cover model after her previous appearance in February 1996 was highly anticipated by fans. Brandy and Cindy Margolis also brought diversity and added appeal to this special edition.

Value

If you’re planning on purchasing this issue as an investment or for future resale value, it is essential to consider its current value in the market. According to collectors’ websites and forums, the July 1999 issue can range from $10-$30 depending on its condition.

Authenticity

With any collectible item, there is always a risk of purchasing counterfeit or fake products. To ensure authenticity, make sure to purchase from reputable sellers or sources such as official Playboy merchandise stores or verified online sellers.

In Conclusion

The July 1999 issue of Playboy is undoubtedly a must-have for any collector or fan of the magazine. Its limited edition status, iconic cover models, and overall rarity make it a valuable addition to any collection. However, make sure to consider its condition, rarity value, cover models choice before making your purchase decision. And remember always to check for authenticity when buying collectible items like this one. Happy collecting!

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Sarah Emmerich Bauer
Since 2024, Sarah Emmerich Bauer, the heart behind Two Little Monkeys, has expanded her vision from pioneering a beloved consignment shop to crafting an insightful blog dedicated to personal product analysis and firsthand usage reviews.

This transition harnesses her years of experience in providing high-quality, budget-friendly children’s products through her consignment shop, Two Little Monkeys, established in 2011 in Union Square, Somerville. Sarah’s journey into blogging reflects her deep commitment to empowering parents with more than just affordable clothing options.

Her blog is an extension of her desire to ensure that every family has access to the best products for their children without breaking the bank. Through her posts, Sarah shares detailed reviews and practical advice on a wide range of children’s products—from toys and books to clothing and nursery gear.