100 books like The Official Preppy Handbook

By Lisa Birnbach,

Here are 100 books that The Official Preppy Handbook fans have personally recommended if you like The Official Preppy Handbook. Shepherd is a community of 10,000+ authors and super readers sharing their favorite books with the world.

Shepherd is reader supported. When you buy books, we may earn an affiliate commission.

Book cover of The National Enquirer: Thirty Years of Unforgettable Images

Maureen Callahan Author Of American Predator: The Hunt for the Most Meticulous Serial Killer of the 21st Century

From my list on American pop culture.

Why am I passionate about this?

Maureen Callahan is a New York Times bestselling author, award-winning investigative journalist, columnist, and commentator. She has covered everything from pop culture to politics. Her writing has appeared in Vanity Fair, New York, Spin, and the New York Post, where she is Critic-at-Large. She lives in New York. For Shepherd, Callahan has selected her favorite books about American pop culture, which is currently dominated by her favorite subgenre, true crime.

Maureen's book list on American pop culture

Maureen Callahan Why did Maureen love this book?

As a child, I loved my grandmother’s visits because she would bring all the tabloids I wasn’t allowed to read — and none was better than The National Enquirer. No other outlet reveled so gleefully in scandal: Hollywood stars, politicians, huckster reverends — all were equal targets, and the Enquirer exposed them the way law enforcement nails suspects: Photographic evidence. Can’t lie your way out of a photo. So here’s a ruddy, paunchy, engaged-to-be-married Sen. Ted Kennedy with his 27-year-old paramour, a Miss Alabama runner-up; married presidential candidate Gary Hart, knocked out of the race after daring the media to catch him cheating — which the Enquirer did, running an exclusive picture of mistress Donna Rice sitting on his lap, Hart incredibly wearing a T-shirt reading Monkey Business; and an unprecedented image that changed tabloid journalism and resulted in the Enquirer’s best-selling issue: Elvis Presley in his coffin at…

By Editors of National Enquirer,

Why should I read it?

1 author picked The National Enquirer as one of their favorite books, and they share why you should read it.

What is this book about?

For more than thirty years, The National Enquirer has put us on a first-name basis with stars, villains, beauties, cads, and killers bringing remarkable stories to life with breathtaking photos that pack an emotional punch and often break news in themselves. This is a sumptuous, mesmerizing selection of the most memorable photos from The National Enquirer history.


Book cover of Careless Love

Maureen Callahan Author Of American Predator: The Hunt for the Most Meticulous Serial Killer of the 21st Century

From my list on American pop culture.

Why am I passionate about this?

Maureen Callahan is a New York Times bestselling author, award-winning investigative journalist, columnist, and commentator. She has covered everything from pop culture to politics. Her writing has appeared in Vanity Fair, New York, Spin, and the New York Post, where she is Critic-at-Large. She lives in New York. For Shepherd, Callahan has selected her favorite books about American pop culture, which is currently dominated by her favorite subgenre, true crime.

Maureen's book list on American pop culture

Maureen Callahan Why did Maureen love this book?

Speaking of Elvis, this biography, the second of two parts, is among the greatest of the late 20th century. We begin with Elvis entering the U.S. Army in 1958 and follow this increasingly lost soul through the years, his fame metastasizing into something unrivaled, incredible, enviable and wholly malignant. Guralnick captures the singular loneliness Elvis came to suffer, the slow suicide that was his Las Vegas residency, the exploitations of his manager, Col. Tom Parker, and a death so humiliating it finally made Elvis what he had longed to be for decades: Profoundly, squalidly human. None other than Bob Dylan called this Presley biography the one that “cancels out all others.”

By Peter Guralnick,

Why should I read it?

1 author picked Careless Love as one of their favorite books, and they share why you should read it.

What is this book about?

Last Train to Memphis, the first part of Guralnick's two-volume life of Elvis Presley, received unprecedented accolades. This concluding volume recounts the second half of Elvis's life in rich and previously unimagined detail, and confirms Guralnick's status as one of the great biographers of our time. Beginning with Presley's army service in Germany in 1958 and ending with his death in Memphis in 1977, Careless Love chronicles the unraveling of the dream that once shone so brightly, homing in on the complex playing-out of Elvis's relationship with his Machiavellian manager, Colonel Tom Parker. It's a breathtaking drama that places the…


Book cover of You'll Never Eat Lunch in This Town Again

Maureen Callahan Author Of American Predator: The Hunt for the Most Meticulous Serial Killer of the 21st Century

From my list on American pop culture.

Why am I passionate about this?

Maureen Callahan is a New York Times bestselling author, award-winning investigative journalist, columnist, and commentator. She has covered everything from pop culture to politics. Her writing has appeared in Vanity Fair, New York, Spin, and the New York Post, where she is Critic-at-Large. She lives in New York. For Shepherd, Callahan has selected her favorite books about American pop culture, which is currently dominated by her favorite subgenre, true crime.

Maureen's book list on American pop culture

Maureen Callahan Why did Maureen love this book?

The New York Times called this memoir “The Hollywood Chainsaw Massacre!” and it still stands as one of the best. Phillips, who died New Year’s Day 2002, was a self-described “nice Jewish girl from Great Neck,” Long Island who loved the movies, movie stars — and books. She was sharp, unsparing, and became the first female producer to win an Oscar for Best Picture. The closest comp title, I think, is The Kid Stays In The Picture by the late Robert Evans, but Phillips does him better in eviscerating no one so much as herself. And this is someone who describes Rolling Stone Ronnie Wood as “very sweet, but . . . smells terrible,” before asking, “Why don’t the English like to bathe?” An observation that could get one canceled today.

By Julia Phillips,

Why should I read it?

1 author picked You'll Never Eat Lunch in This Town Again as one of their favorite books, and they share why you should read it.

What is this book about?

“The Hollywood memoir that tells all . . . Sex. Drugs. Greed. Why, it sounds just like a movie.”—The New York Times
 
Every memoir claims to bare it all, but Julia Phillips’s actually does. This is an addictive, gloves-off exposé from the producer of the classic films The Sting, Taxi Driver, and Close Encounters of the Third Kind—and the first woman ever to win an Academy Award for Best Picture—who made her name in Hollywood during the halcyon seventies and the yuppie-infested eighties and lived to tell the tale. Wickedly funny and surprisingly moving, You’ll Never Eat Lunch in This…


Book cover of The Vanity Fair Diaries: Power, Wealth, Celebrity, and Dreams: My Years at the Magazine That Defined a Decade

Maureen Callahan Author Of American Predator: The Hunt for the Most Meticulous Serial Killer of the 21st Century

From my list on American pop culture.

Why am I passionate about this?

Maureen Callahan is a New York Times bestselling author, award-winning investigative journalist, columnist, and commentator. She has covered everything from pop culture to politics. Her writing has appeared in Vanity Fair, New York, Spin, and the New York Post, where she is Critic-at-Large. She lives in New York. For Shepherd, Callahan has selected her favorite books about American pop culture, which is currently dominated by her favorite subgenre, true crime.

Maureen's book list on American pop culture

Maureen Callahan Why did Maureen love this book?

Londoner Tina Brown alights in New York City and falls fast and hard for power-playing, the machinations of billionaires and politicos, the trappings of glamour and wealth and the city itself, whose rococo sensibility she brings to Vanity Fair, a magazine she rescues from irrelevance and turns into a monthly-must read. Brown generated national headlines with her high-low sensibility and indelible cover images (a naked and pregnant Demi Moore scandalized middle America, much to Brown’s delight). She also writes about her guilt as a working mother, the thrill of matching the right journalist to the right story, and her trepidation in fighting for the salary she knew she deserved. A witty and colorful document of the last moment magazines really mattered.

By Tina Brown,

Why should I read it?

1 author picked The Vanity Fair Diaries as one of their favorite books, and they share why you should read it.

What is this book about?

'Indiscreet, brilliantly observed, frequently hilarious' Evening Standard
'Hang on - it's a wild ride' Meryl Streep

It's 1983. A young Englishwoman arrives in Manhattan on a mission. Summoned in the hope that she can save Conde Nast's troubled new flagship Vanity Fair, Tina Brown is plunged into the maelstrom of competitive New York media. She survives the politics and the intrigue by a simple stratagem: succeeding.

Here are the inside stories of the scoops and covers that sold millions: the Reagan kiss, the meltdown of Princess Diana's marriage to Prince Charles, the sensational Annie Leibovitz cover of a gloriously pregnant,…


Book cover of The United States of Epic Fails: 52 Crazy Stories and Blunders Through History That You Didn't Get Taught in School

David P. Barash Author Of OOPS! The Worst Blunders of All Time

From my list on people making mistakes: mythic, silly, tragic.

Why am I passionate about this?

I’m an emeritus professor of psychology (University of Washington) who has long been intrigued by the mistakes that people have made throughout history. I’ve long been struck by Oppenheimer’s observation, immediately after the Trinity explosion, that “I am become Death, the destroyer of worlds.” This led me to look into the wide array of mistakes, from the mythic, literary, athletic, business, political, medical, and military. In writing OOPS!, I let myself go in a way that I’ve never before, writing with a critical and wise-ass style that isn’t strictly academic, but is factually accurate and, frankly, was a lot of fun!

David's book list on people making mistakes: mythic, silly, tragic

David P. Barash Why did David love this book?

This is an accessible account of history through the lens of how “mistakes were made,” and how most of us aren’t told about them.

It is plain old-fashioned great fun to read about blunders in the worlds of business, sports, pop culture, even some of America’s epic military failures (so long as they happened long ago!). A great corrective to claims that the US is uniquely blessed with perfection.

By Bill O'Neill,

Why should I read it?

1 author picked The United States of Epic Fails as one of their favorite books, and they share why you should read it.

What is this book about?

Have you ever wondered what the biggest failures in American history are?

Which sports teams just can’t seem to catch a break and keep failing, over and over and over in the most disastrous manner?

What are some of the biggest failures in American pop culture?

In The United States of Epic Fails: 52 Crazy Stories and Blunders Through History That You Didn't Get Taught in School you’ll learn all about these embarrassing moments and many other American failures on an epic level.

Here you will find out:

What film almost destroyed a major studio and killed a movie genre?…


Book cover of Where the Girls Are: Growing Up Female with the Mass Media

Susan Bordo Author Of TV

From my list on popular culture.

Why am I passionate about this?

I was born in 1947, in the first wave of the baby boom, and was part of the first generation to grow up immersed in television, movies, and popular music. I have always felt the force of pop culture in my life.  But it was only at a certain point that it became something that I felt I could write about and be taken seriously. Writers like Pauline Kael made it possible for me because they obviously adored popular culture but they neither puffed it up nor dumbed it down. They wrote about it with intelligence, honesty, and curiosity and also as a barometer of where people were at and where society was going. That’s what I’ve aimed at in my own writing, from my books on the male and female body to those on politics and the media to my most recent exploration of the impact of television on our lives.

Susan's book list on popular culture

Susan Bordo Why did Susan love this book?

Where the Girls Are is about a particular generation of women growing up in post War America, and the impact popular media had on their lives, both for good and for bad. It weaves wonderfully smart, often funny, always engagingly written discussions of pop music, movies, and television shows with Douglas’s own experiences at the time. It’s unabashedly feminist—but it isn’t a speech or a political manifesto. It’s an exploration of the push-pull of growing up female at a transitional time, a time in which attitudes toward women were changing, unevenly, and how pop culture reflected the tensions of the times. This book is history, memoir, sociology, media studies, all at once – immensely informative and very entertaining.

By Susan J. Douglas,

Why should I read it?

1 author picked Where the Girls Are as one of their favorite books, and they share why you should read it.

What is this book about?

Media critic Douglas deconstructs the ambiguous messages sent to American women via TV programs, popular music, advertising, and nightly news reporting over the last 40 years, and fathoms their influence on her own life and the lives of her contemporaries. Photos.


Book cover of Night Shift

Kenya Moss-Dyme Author Of Daymares

From my list on horror that deliver the most bang for the bite.

Why am I passionate about this?

Like most writers, I’ve been a voracious reader since I was a child; but my preferences were witches and haunted houses, rather than princesses and talking frogs. As I developed my own writing, I wanted to tell stories that were reflective of my world but with a dark twist. My first completed story was "Patchwork", about a woman emptying the marital home after the breakdown of her marriage. I went on to participate in several popular horror anthologies. I really enjoy the challenge of writing a great short story because you have to get the reader in a chokehold early and then deliver that gut punch sooner than later.

Kenya's book list on horror that deliver the most bang for the bite

Kenya Moss-Dyme Why did Kenya love this book?

Originally published in 1978, I was still a bit young to be devouring such dark and twisted tales but this one became my own blueprint for writing short stories.

This wasn't my first SK book, I had previously read his other novels like Salem's Lot and The Stand. But once I discovered Night Shift, it was like getting a different story each and every time I opened the book. 

There are no 'favorites' here because each one is sublime, but if I were forced to select 2-3 out of the 20, I'd go with "Gray Matter", "The Mangler", and "Sometimes They Come Back", mostly because these have quotes that I still see and use here and there, some 40 years later.

By Stephen King,

Why should I read it?

3 authors picked Night Shift as one of their favorite books, and they share why you should read it.

What is this book about?

Stephen King’s first collection of short stories, originally published in 1978, showcases the darkest depths of his brilliant imagination and will "chill the cockles of many a heart" (Chicago Tribune). Night Shift is the inspiration for over a dozen acclaimed horror movies and television series, including Children of the Corn , Chapelwaite, and Lawnmower Man.

Here we see mutated rats gone bad (“Graveyard Shift”); a cataclysmic virus that threatens humanity (“Night Surf,” the basis for The Stand); a possessed, evil lawnmower (“The Lawnmower Man”); unsettling children from the heartland (“Children of the Corn”); a smoker who will try anything to…


Book cover of The Birth of Korean Cool: How One Nation Is Conquering the World Through Pop Culture

Bruce and Ju-Chan Fulton Author Of Mina

From my list on Hell Chosŏn.

Why are we passionate about this?

A couple who have been claimed by Korea—Bruce as a US Peace Corps volunteer there and Ju-Chan as a native Korean and an English teacher—and its culture, society, history, and especially literary heritage. We have been translating modern Korean fiction into English since 1980. Bruce was fated to become involved with Korean literature by virtue of being born on October 9, the day in 1446 when Great King Sejong promulgated (officially announced) the creation of the Korean alphabet, hangŭl, to the people of Korea.

Bruce's book list on Hell Chosŏn

Bruce and Ju-Chan Fulton Why did Bruce love this book?

At a time when academics tend to look down their noses at Korean popular culture (Hallyu, literally “the Korean wave”), which in recent years is driving popular culture worldwide, The Birth of Korean Cool is a refreshing analysis based on the supposition that Korea is finally “getting even” with the rest of the world for being underappreciated for thousands of years.

By Euny Hong,

Why should I read it?

1 author picked The Birth of Korean Cool as one of their favorite books, and they share why you should read it.

What is this book about?

A FRESH, FUNNY, UP-CLOSE LOOK AT HOW SOUTH KOREA REMADE ITSELF AS THE WORLD'S POP CULTURE POWERHOUSE OF THE TWENTY-FIRST CENTURY

By now, everyone in the world knows the song "Gangnam Style" and Psy, an instantly recognizable star. But the song's international popularity is no passing fad. "Gangnam Style" is only one tool in South Korea's extraordinarily elaborate and effective strategy to become a major world superpower by first becoming the world's number one pop culture exporter.

As a child, Euny Hong moved from America to the Gangnam neighbourhood in Seoul. She was a witness to the most accelerated part…


Book cover of Documentary Expression and Thirties America

Scott Borchert Author Of Republic of Detours: How the New Deal Paid Broke Writers to Rediscover America

From my list on the New Deal’s contributions to the arts.

Why am I passionate about this?

My great uncle was an eccentric book collector who lived in an old, rambling house stuffed floor-to-ceiling with thousands and thousands of books. After he died, I inherited a tiny portion of his collection: a set of state guidebooks from the 1930s and 40s. These were the American Guides created by the Federal Writers’ Project, the New Deal program that put jobless writers to work during the Great Depression. I dipped into these weird, rich, fascinating books, and I was hooked immediately. Some years later, I quit my job in publishing to research and write my own account of the FWP’s unlikely rise and lamentable fall, Republic of Detours

Scott's book list on the New Deal’s contributions to the arts

Scott Borchert Why did Scott love this book?

This is a scholarly work, but don’t let the unassuming title fool you: Stott’s writing is crisp, elegant, and highly readable, and his insights are crucial to any understanding of the New Deal’s place in American culture. He covers the Roosevelt administration’s cultural undertakings—from the WPA projects to Farm Security Administration photographers to FDR’s own political style and “documentary imagination”—but his real subject is the broader documentary impulse that was expressed so forcefully and variously during the 1930s. This impulse was hardly confined to the federal government’s interventions in the arts. The connections he draws between the New Deal and, say, Martha Graham’s dance productions, or James Agee and Walker Evans’s Let Us Now Praise Famous Men, are illuminating and convincing. 

By William Stott,

Why should I read it?

1 author picked Documentary Expression and Thirties America as one of their favorite books, and they share why you should read it.

What is this book about?

"A comprehensive inquiry into the attitudes and ambitions that characterized the documentary impulse of the thirties. The subject is a large one, for it embraces (among much else) radical journalism, academic sociology, the esthetics of photography, Government relief programs, radio broadcasting, the literature of social work, the rhetoric of political persuasion, and the effect of all these on the traditional arts of literature, painting, theater and dance. The great merit of Mr. Stott's study lies precisely in its wide-ranging view of this complex terrain."-Hilton Kramer, New York Times Book Review

"[Scott] might be called the Aristotle of documentary. No one…


Book cover of Consuming Religion

Chad E. Seales Author Of Religion Around Bono: Evangelical Enchantment and Neoliberal Capitalism

From my list on American evangelicalism and neoliberal religion.

Why am I passionate about this?

I've always been fascinated by the ways religion reconciles contradiction. Both of my parents were public school teachers in the panhandle of Florida, and I now work at a public university in Texas, yet the culture in which I was raised, of white evangelicalism, supported economic policies of neoliberalism that defunded public life. My interest in American religion is motivated by the question of why we participate in systems that harm us. This is an economic question, but sufficient answers must address the power of religion to shape what we see as morally good and bad. These books all do that.

Chad's book list on American evangelicalism and neoliberal religion

Chad E. Seales Why did Chad love this book?

If you want to understand how corporations and not churches became the most powerful institutions of moral influence in America, capable of taking away an employee's personal choice outside the workplace and denying their access to healthcare based on the owners’ biblical beliefs, legally protected by the U.S. government as a religious freedom, then you need to read this book.

By Kathryn Lofton,

Why should I read it?

1 author picked Consuming Religion as one of their favorite books, and they share why you should read it.

What is this book about?

What are you drawn to like, to watch, or even to binge? What are you free to consume, and what do you become through consumption? These questions of desire and value, Kathryn Lofton argues, are at bottom religious questions. Whether or not you have been inside of a cathedral, a temple, or a seminary, you live in the frame of religion. In eleven essays exploring soap and office cubicles, Britney Spears and the Kardashians, corporate culture and Goldman Sachs, Lofton shows the conceptual levers of religion in thinking about social modes of encounter, use, and longing. Wherever we see people…


5 book lists we think you will like!

Interested in pop culture, pop music, and civilization?

10,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about pop culture, pop music, and civilization.

Pop Culture Explore 148 books about pop culture
Pop Music Explore 47 books about pop music
Civilization Explore 211 books about civilization