Playboy Classics

Dear Playboy Advisor: I Love Small Dick Humiliation

December 12

Once a Playmate, Always a Playmate

December 11

20Q: Diane Guerrero

December 10

The Playboy Interview With Anita Bryant

December 9

Playboy Fiction: The Domestic Lives of Superheroes

December 6

Dear Playboy Advisor: My Friends Think My Kink Is Weird

December 5

Playmate Q&A: Kennedy Summers

December 4

20Q: Lorenza Izzo

December 3

The Playboy Interview With Charles Evers

December 2

Playboy Fiction: The Darkness in the Backroom

November 29

Dear Playboy Advisor: My Girlfriend Wants Too Much Sex

November 28

Playmate Q&A: Jessica Wall

November 27

20Q: Liz Cambage

November 26

The Playboy Interview With Eddie Murphy

November 25

Playboy Fiction: The Sparrow

November 22

Playboy Advisor: How to Give an Amazing Blowjob

November 21

Playmate Q&A: Shelby Rose

November 20

20Q: Sofia Boutella

November 19

Playboy Fiction: Grunge

November 15

Playmate Q&A: Amelia Talon

November 13

20Q: Aubrey Plaza

November 12

The Playboy Interview With Sharon Stone

November 11

Playboy Fiction: Babylon

November 8

Playmate Dominique Jane Is Proud to Be Part of Playboy Revolution

November 6

20Q: Danica Patrick

November 5

The Playboy Interview With Bernie Sanders

November 4

Playboy Fiction: Cecily

November 1

Playmate Q&A: Elizabeth Leigh Sullivan

November 1

Dear Playboy Advisor: I’m Too Ashamed of My Body to Have Sex

October 31

Playmate Q&A: Brook Power

October 30

20Q: Anna Kendrick

October 29

The Playboy Interview: Stephen King

October 28

Playboy Fiction: The Disgruntled Americans

October 25

Dear Playboy Advisor: How Do I Bring Up Pegging?

October 24

Playmate Pride: Gillian Chan

October 23

20Q: Halsey

October 22

The Playboy Interview With Jim Carrey

October 21

An Open Letter to Men Who Insult Women’s Looks

October 20

Was Marge Simpson in Playboy?

October 20

What Should Porn for Women Look Like? Bellesa Knows

October 19

Playboy Fiction: Hush Puppies

October 18

Playmate Q&A: Khrystyana

October 16

Playmate Katie Vernola Is Burning Up the Racetrack

October 15

The 1992 Playboy Interview With Robin Williams

October 14

Celebrate National Coming Out Day 2024 with Playboy

October 11

Playboy Fiction: A Beautiful Country

October 11

20Q: Halle Berry

October 8

The Playboy Interview With Jerry Seinfeld

October 7

How Athlete Bekka Hauri Blends Beauty, Brains And Ball

October 4

The Junkyard Shootout: Beauty in the Breakdown

October 4

The Playboy Interview With Jimmy Carter

October 1

20Q: Kaley Cuoco

October 1

The Playboy Interview With Pete Rose

October 1

The Playboy Interview With Whoopi Goldberg

September 30

Playboy Fiction: Uncle Andy Gee’s Farewell Show

September 27

The Playboy Advisor: Is the Missionary Position Boring?

September 26

20Q: Kehlani

September 24

The Playboy Interview With Dolly Parton

September 23

Personal Visions of the Erotic

September 21

Playboy Fiction: Here’s What I Want You to Do

September 20

Dear Playboy Advisor: Can I Keep My Exes’ Erotic Photos?

September 19

Playmate Geena Rocero Shares a Special Recipe

September 18

20Q: Daniel Radcliffe

September 17

The Playboy Interview With Chris Rock

September 16

Playboy Fiction: Finishing

September 13

Dear Playboy Advisor: Is There a Cure for Premature Ejaculation?

September 12

Playmate Pride: Geena Rocero

September 11

Playboy Fiction: ‘Olive Days’

September 10

20Q: Harry Edwards

September 10

Yes, Your Home Can Destroy Your Love Life

September 8

The Playboy Interview With Charles Barkley

September 7

Playboy Fiction: The Filmmaker

September 6

The Playboy Interview With Ben Affleck

September 5

Dear Playboy Advisor: How Do I Achieve My Dildo Dreams?

September 5

Playmate Pride: Teela LaRoux

September 4

20Q: Patrick Stewart

September 3

The Playboy Interview With Scarlett Johansson

September 2

Playboy Fiction: Adam’s Apple

August 30

Dear Playboy Advisor: My Partner Makes More Money Than Me, and It Bothers Me

August 29

The Beauty of Inspiration: A Conversation With March 2019 Playmate Miki Hamano

August 28

20Q: Maren Morris

August 27

The Playboy Interview With Cheech and Chong

August 26

Playboy Fiction: Subtract One Death

August 23

9 Things to Know About March 2018 Playmate Jenny Watwood

August 21

The Secrets to Finding Great Sex While Traveling Solo

August 20

20Q: Dax Shepard

August 20

The 1990 Playboy Interview With Donald Trump

August 19

Playmate Pride: Ashley Hobbs

August 14

20Q: Cillian Murphy

August 13

The Playboy Interview With Keanu Reeves

August 12

Playboy Fiction: The Music Room by Steven King

August 9

Dear Playboy Advisor: Can Weed Help Me Revive My Sex Life?

August 8

Get to Know 1976 Playmate of the Year Lillian Müller

August 7

The Playboy Interview With Salvador Dali

January 18

The Playboy Interview With John Mayer

January 28

The Playboy Interview With Spike Lee

January 10

The Playboy Interview With Willie Nelson

October 15

The Playboy Interview With Snoop Doggy Dogg

October 15

Dear Playboy Advisor: How Do I Unlock the Pleasure of the Prostate?

October 15

The Playboy Interview With Ray Kurzweil

September 3

Playboy Fiction: Francophile

August 31

20Q: Paul Rudd

February 10

The Playboy Interview With Dwayne Johnson

October 21

Dear Playboy Advisor: Is It Normal to Think About Sex 24/7?

April 22