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Sleeping With Bad Boys: A Juicy Tell-All of Literary New York in the 1950s and 1960s

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Alice Denham's lusty memoir is a juicy tell-all about a time when male writers were gods and an aspiring and gorgeous female novelist tries to win respect—and sometimes more. Caught between the sheets are James Dean, Norman Mailer, Hugh Hefner, Philip Roth, and William Gaddis. The steam rises page by page as Denham — the only Playboy Playmate to have her fiction published in the same issue as her centerfold—chases her dream of writing as a young, oversexed beauty in the literary swirl of 1950s Greenwich Village, New York City.

256 pages, Paperback

First published November 7, 2006

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About the author

Alice Denham

10 books16 followers
Alice Denham (born January 21, 1933 in Jacksonville, Florida) is an American model, writer and scholar. She was Playboy magazine's Playmate of the Month for the July 1956 issue. Her centerfold was photographed by Mike Shea and Lawrence Tirschel. Denham posed for other men's magazines during her modeling career, but she was as well known for her academic achievements as for her physical attributes. She earned a bachelor's degree from the University of North Carolina in 1949 and a master's degree from the University of Rochester in 1950, and is a member of the Phi Beta Kappa society. Her writing talents were obvious to Playboy; several Playmates have written the text that accompanied their pictorials, but Denham is the only Playmate to have written a short story that was published in the same issue as her centerfold. Denham pursued a career in writing and education. She's written several short stories and novels, including Amo and My Darling from the Lions, and taught creative writing at the City College of New York, where she served as an adjunct professor of English from 1970 to 1980. She also held fiction-writing seminars at the University of Toronto for several years. According to The Playmate Book, she has completed her memoirs and also is writing a non-fiction book about her family's "migration from South Carolina and Scotland to Florida at the time of the Seminole Indian Wars."

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5 stars
32 (26%)
4 stars
36 (29%)
3 stars
38 (31%)
2 stars
13 (10%)
1 star
2 (1%)
Displaying 1 - 30 of 30 reviews
Profile Image for Jonathan.
1,009 reviews1,229 followers
December 11, 2013
Hey you! Yes YOU!

Want to know how good David Markson is in bed?
Or William Gaddis?
Want to be able to compare the penis sizes of your favorite literary bad-boys (i.e. the complete and total assholes - I will give you a hint - you will not be surprised to find that the more aggressively misogynistic they are, the less they have in their trousers)?
Want to read the story of an intelligent, creative, interesting woman trying to fight her way through all this crap?
Then this is for you...

It is not some sort of literary masterpiece, and is not pretending to be. What it is, actually, is an exploration of that transient period in 50's New York, where the position of women, and the roles available to them, was just starting to change.

Alice did nude modelling to make time to write. She slept with lots of interesting men because she wanted to. She tried to write in a way she felt was important and was told again and again by male editors that her characters had too much"penis envy" and she should just shut up and give them a blow job...

I think she is pretty awesome.

And I think this looks like it needs unBURYING https://www.goodreads.com/book/show/1...
Profile Image for Roxy.
5 reviews1 follower
August 16, 2007
I must start by saying that the edition of this book that I read was the uncorrected proofs (the gods grace us in SF with used book stores that are the envy of the world); therefore some of what I might find to be 'flaws' could possibly be corrected in a the final version.

Her style and voice is daring and true, the vernacular chosen is that of the times and her vocabulary shines refreshingly.
Her wit lends to smirking smiles from the reader and her triumphs and rejections are heartfelt. She bares all (in a few ways) and takes a bold stand on the time, being a writer and a woman - in love, in life, in passion.
What might come off as 'risky' even today in certain circles is just further proof of her 'no holds barred' attitude. Personally, I enjoyed reading about how Jimmy Dean was in bed since there is no chance of that for myself. But I do wonder if some of the men still living might think of her sizing them up in ink...
I will say being a short brunette with a sporadic lifestyle, unhinged love life,and the writing curse I related much to the author and her story.
This memoir is just that, with a tip of the hat to certain past friends as well as a sneering last word to those whom she may not have yet been able to say.

One draw back, of very few, would be her re-accounting of events aforementioned - perhaps this is to keep the reader up to speed, but for those of us who pay attention it becomes somewhat trivial. The bouncing of dates and times and what happened when and then returning to 55 from 64 - is well laid out, but slightly rough - and could have been better polished in the final version. As mayhaps the ending which comes somewhat abruptly from such a fine a build and progression - but so it goes, perhaps that was all she felt the need to tell.

All and all a fantastic read, especially for those much enamored and involved with the literature, writing style and lives of the time. I highly recommend it. And much Kudos to the Miss Denham; I'd love to have a drink with her.
Profile Image for Justine.
Author 9 books201 followers
June 30, 2008
What kept me reading wasn't so much the 'gossip' -- these writers were macho? they drank and slept around? really? -- but the description of a young, determined, rebellious woman with 'man-sized' ambition negotiating her way through a world that seems both antiquated and disturbingly close. As a woman with a determined, rebellious, ambitious nature herself, this book tripped off some sympathy and resonance --and deep relief that her world is not mine.
Profile Image for Asails F.
75 reviews37 followers
February 7, 2011
I Met Alice in the Barnes and Noble at Union Square. She was wonderfull and she signed my book. She spoke regretfully of Bill Gaddis.

I told her how my Uncle Bill showed up at my house with Ethel "Ethyl" Merman who used to sing while my Grandfater played the piano. Ethel just bragged about finishing with her "shortest marriage ever." She was not too happy. They were both extremely drunk and it was 3AM. Ethel sang and complained moare about Borgnine.

I realized after reading her book that Uncle Bill had just left Alice alone in the middle of the night, but his druckenness that night was normal.

Later I assured her that she was better off and that she still looked tremendous... After asking her to dinner she had to add "but I am married." The offer is still open and it would be great to take them both to dinner.

Alice was the first to show up in pictures in Playboy and in the same issue publish a story. She's amazing!
40 reviews
April 18, 2011
Not a lurid memoir, a frank feminist account of the author's life as struggling NYC writer in the male-dominated literary world of 1950s and 1960s. The author is a nude model to afford to live in NYC while having time to write as much as possible while many of her male peers had cushy industry jobs to do the same. She discusses the 'wild' NYC art scene and her own sex life frankly and sometimes with an excellent writers turn. The occasional inspired turns of phrase and descriptions save it from a 3 star review.
Profile Image for Camille.
6 reviews
August 22, 2010
Met the author in SMA and bought the book from her. This is much more than just her escapades -- she portrays the conflicts faced by women in the 50s and 60s.
Profile Image for Rex Fuller.
Author 7 books184 followers
February 17, 2016
Alice Denham
BA North Carolina ‘49
Phi Beta Kappa
MA, Rochester, ‘50
Playmate, July ‘56
Author: novels, “My Darling from the Lions” ‘67, and “Amo” ‘74; memoirs “Sleeping with Bad Boys” ‘06, and “Secrets of San Miguel” ‘13; and numerous short stories

Wait. Playmate? And novelist? Hmmm. Might be something here. Throw in nude model for hundreds of commercial and amateur photo shoots. Okay, tell me more.

Lovers: James Dean (Rebel Without a Cause), James Jones (From Here to Eternity), Philip Roth (Goodbye Columbus), William Gaddis (The Recognitions), and scores of others.

Friends: James Baldwin (Go Tell It on the Mountain), Norman Mailer (The Naked and the Dead), Katherine Anne Porter (Ship of Fools), Rubin Hurricane Carter (successful middleweight boxer wrongly convicted of murder, released after 20 years, subject of ‘99 film The Hurricane), plus hundreds of others.

She was the Sixties during the Fifties. Denham’s story crackles and she doesn’t flinch from the details (some graphic) of her struggle to survive while writing in New York – before women were considered equal. This will surprise you how good it is.
Profile Image for Dada.
8 reviews1 follower
March 5, 2016
What a nice surprise! I started reading it with very low expectations expecting a brainless tell all story and instead I discovered a brainy memoir written in a philosophical slangy, seductive, honest, entertaining and thought-provoking way. It contains a trove of priceless historical anecdotes and heartbreaking account of what it meant to be a female writer in the era of the giant male literary lions of the 50s and 60s in New York.
Profile Image for Candice.
394 reviews6 followers
March 14, 2023
This is interesting insofar as the New York scene in the 50's, but after about a third of the way through the book, I got tired of Alice's exploits. It's a tell all memoir mostly about the famous characters she was sleeping with, but I lost patience with it although I respect her ability to burn through the sexual mores of the time.
Profile Image for David Goode.
16 reviews2 followers
December 21, 2016
Wow!!! I'm nominating the late Alice Denham for immediate cult status.Everyone has a story.Some are just more interesting than others.Ms.Denham has one of the more interesting ones.She has written for The NY Times,New York Magazine,Cosmopolitan and The Village Voice.As well as having written 3 novels.She also famously had a short story published in the July 1956 issue of Playboy.The same issue in which she was Playmate of the Month.
Her memoirs about the time she spent modelling for artists,camera clubs,the covers of men's sweat mags and just about everything else while living in NY's Greenwich Village pursuing her ambition to be a writer in the 50s is what makes this book so fascinating.And of course you'll read about her relationships with "bad boys".I highly recommend this book.

Profile Image for Noreen Anastasia.
333 reviews
April 11, 2018
I think the title of this book did it an injustice. The novel is much more about Alice trying to get her writing published, building relationships to do so, her love of literature, and her love of booze. There's a distinct chance I liked it so much because I can relate. There's no shame in sleeping around, no shame in bodies, and certainly no shame in trying to get work published. There was a bit of repetition with stating how much she loves drinking and talking literature, but boy can I relate. There may have been a bit of glossing over how many nude photo shoots she did, but girl had to get by. On the whole, I recommend.
Profile Image for Kate Schwarz.
953 reviews17 followers
April 1, 2016
What an odd book. It promises to be a seedy tell-all but really it just made me sad for Alice, who wanted so badly to be taken seriously as a writer but modeled nude too many times for that to happen. Should she have had to choose? I dunno. But she claims to be "pals" with many of the big-hitters of the literary scene of the 1950s and 1960s but when her novel FINALLY was published, absolutely none of these "pals" came through to for her to review it, write up a blurb about it for the jacket, and support her. Poor Alice!
Profile Image for Rebecca.
83 reviews8 followers
July 4, 2008
I love this book. New York city seemed so exciting and vivid I could smell the streets and bars. Reminded me of the movie "Sweet Smell of Success"
The writers she met used her, she was young, beautiful, liked to drink and loved men. She describes her stable of partners with a sense of humor and never apologizes for loving sex.
Hugh Hefner's chapter was amusing, his personality is as wooden as his smile.
This book was very fun to read.
Profile Image for Anna A-P.
67 reviews
June 17, 2019
I discovered Alice after reading her obituary in the New York Times. My dear fellow Southern lady friend gave to me, and it was a perfect gift. So much of Alice's life resonated with me as a Southern gal moving to a big city, as well (unfortunately) as navigating double standards for women and fighting for reproductive justice. Highly recommend!
Profile Image for Dale Stonehouse.
435 reviews9 followers
March 6, 2012
Three stars for the writing, disjointed at times but compelling. A fourth star for what I learned about life as a career woman in 1950s and 60s USA. That culture is pretty disgusting to contemplate for a father with three daughters. Lots of celebrity dirt for those so inclined.
431 reviews5 followers
January 12, 2022
"Sleeping With Bad Boys" seemed like it would be a light but interesting memoir, but it grew on me. Better known, perhaps, for being a Playboy centerfold and a nude or semi-nude model in the 50s and 60s, Denham reveals, convincingly, that she modeled mainly because it was the fastest way to make money to support her desire to be a writer. (She also had a short story published in that self-same Playboy issue, the only woman in history with that particular centerfold/author achievement.)

But as her title suggests, there's more to the story. Denham loved sex, and was unabashed about it in the 50s. Her social and sometimes sexual circle included James Dean before he was famous and a variety writers, including James Jones, William Gaddis, Norman Mailer and Philip Roth. She kisses. She tells. The story goes that when Roth heard that this book was about to be published, he fretted over how good a lover he would appear to be. (Quite passionate, said Denham.). She never slept with Mailer, she notes, but they were friends for a good long while.

As she got older, and modeling seemed both less desirable and less successful, Denham finished her first novel and struggled trying to get it published. The tone of the tale shifts to her writerly side, and I found myself rooting for her.

In the end, this is a charming memoir of a woman who was well ahead of her time. Check out her New York Times obituary.
19 reviews
September 28, 2023
This book was given to me by a friend with similar taste and interests, but i still had an impression that it would be a seedy, sordid tell-all of substandard quality. As it turned out it was the complete opposite. Alice Denham is a masterful writer who has lived an extraordinary life and has a knack for story telling.

She tells an amazing story throughout, but I most enjoyed the the first third of the book in which she described how, as a young adult she broke with her parents and made a bold decision to move to New York City and making a go of it as a professional writer. She goes on to give a fascinating account of New York City in the late 40s and early 50s, when Norman Mailer was sowing his oats and co-founded the Village Voice

Her subsequent experiences with years of hard work, modeling by day and writing by night show her dedication to her calling, energy and discipline with which she broke through to get herself a book deal by the 1970s.

Denham is a great power of example for young writers everywhere. Not only because she has an intriguing and inspirational story to tell, but more so because of how she tells it. Denham is completely honest, straightforward and unabashed in the telling. She knows who she is and represents herself with a grace and dignity that show she knows herself well and has transcended the norms and mores imposed during her upbringing and of the 50s era. That's truly a lesson for us all
Profile Image for manatee .
266 reviews3 followers
June 7, 2023
I wish I could say some great things about this book but I really can’t. While the author comes across as a very likable main character and her sexual escapades are mildly interesting the book jumps around all over the place.The narrative just isn’t tight enough.
Alice’s single minded determination to make it as a writer is really compelling. She has to sacrifice decent paying jobs, relationships, family life so she can finish her novel and call herself a writer. In the end , was it really worth it? If she worked so hard at her craft , why isn’t the writing better? Why did she come up with sentences like “ But I was there to suck wisdom’s teat and she wanted it sucked.” Actually that stinker of a sentence blemishes an otherwise fine reminiscence about Alice’s friendship with Katherine Anne Porter. Still, I’m looking forward to reading My Darling From The Lions. Perhaps her novel will be better? I do think someone should write an academic article on this writer as her life was so interesting.
Profile Image for Julene Matthews.
114 reviews3 followers
March 28, 2022
Very readable and quick flowing. She tells of her time modelling and writing in New York in the 1950's and 1960's . The modelling was mainly nude, so lots of saucy descriptions and in a couple of cases, liasons with her clients. She modelled to support herself while writing her books. She appeared in Playboy.
There is a loose chronological thread of her story based around relationships with family and her affairs.
I couldn't help thinking of the Mad Men series as it is a similar era.
She meets up with other well known authors of the time Norman Mailer,Phillip Roth plus Hugh Hefner, James Dean, JFK and other celebrities.
I actually googled her and discovered most of this ACTUALLY happened. There are photos in the book as well.
Profile Image for Jeremy Hornik.
829 reviews21 followers
September 30, 2024
Fun and trrrrashy! Which famous novelist had a small penis and liked going down on women? What’s nude modeling for an amateur camera club like? What was Hef like in the sack? Plus, it doubles as a mid-20th century survey of American literature. Ms. Denham is a resolute artist and adventuress, an early feminist and an independent thinker.

It is rather shocking that the book more or less ends with the great victory: legalization of abortion. Yeah, huh. To paraphrase Virginia Slims, we fell a long way, baby.
Profile Image for Zelmer.
Author 12 books47 followers
April 1, 2021
I enjoyed reading this memoir. I plan on reading more of Miss Denham's books.
Profile Image for Eric W.
156 reviews11 followers
December 14, 2025
Although it was interesting to read about her relationships with mid-century notables such as James Dean and Hugh Hefner, I got bored halfway through and skimmed the rest.
Profile Image for Andy.
Author 18 books153 followers
July 21, 2008
She looks like a girl I used to date. That's an instant sell...I'm being a shallow bastard today, haha.
Okay, I finished the book. While Denham's tell-all isn't as mind-bogglingly awful as fellow Playmate Pamela Anderson's "Star" it's almost there. I'm amazed that a cheesecake model thinks she can be taken seriously as a high-brow author. Then again, I can't imagine an Austrian body builder becoming Governor of California, so who knows? It's a bad book, folks.
Profile Image for Nicole.
247 reviews26 followers
February 2, 2009
I found this book very readable and fast-paced.

So why, you may ask, am I giving it a three?

In a lot of sections of this book, the time being recounted slips off kilter. Is an event taking place in 1953 or 1963? It's often hard to tell. Her asides are often long-winded and irrelevant to the event at hand, taking you out of the story she's in the midst of telling, and making it hard to get back into it.

I did find this engaging, but also frustrating.
Profile Image for Joyce.
816 reviews22 followers
October 23, 2016
i read this book as part of my research on gaddis, it's useful for a woman's eye view on what life was like at the period, and it's good to know bill was a better man than almost any of the others mentioned. but Denham's writing is often clunky and she repeats herself often. i feel like her publisher (who on looking up mostly focus on books about gambling) probably asked her insert a bunch of unnecessary lurid details so they could market this as a sexy book
Profile Image for Jennifer.
14 reviews
July 16, 2007
I skimmed this. The writing is pretty lousy, but the gossip is pretty juicy. Too juicy sometimes. She periodically inserts Penthouse Forum-esque accounts of getting it on with various writers. And the writing doesn't flow well. But the Mailer bits were (of course) interesting to me. And some of the other bits were as well. I do not recommend the book on the whole.
Profile Image for Stella.
156 reviews17 followers
January 26, 2020
This is so much more than a tell-all about sexual escapades. While those details were certainly interesting, the most intriguing part of her story was her relentless pursuit of becoming a published author in 1950's New York. Denham was unapologetically her own brand of feminism.
78 reviews
August 30, 2012
Really different times, can't relate, but she was really something else.
Profile Image for Julene.
358 reviews4 followers
April 13, 2014
Her storytelling involves too much meandering; this is a cool story, but I don't need every detail included.
Displaying 1 - 30 of 30 reviews

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