A cultural giant for more than 60 years, today Hugh Hefner celebrates his 91st birthday from a unique position: that is, being able to watch his life story play out on TV in Amazon’s new original docu-series American Playboy: The Hugh Hefner Story, the first episode of which you can stream for free here. Today, the idea that the magazine—once little more than a notion in the mind of a frustrated 25-year-old copywriter—was ever anything less than a symbol of sex, style and sophistication now seems like a funny dream.

But it takes more than the blink of an eye to build something historic, so we’ve taken the liberty of charting out the meteoric trajectory of the Playboy brand and the man behind it with 91 facts about the original Mr. Playboy.

We at Playboy.com offer you our sincerest wishes of happiness on your 91st birthday, Hef. Cheers!

  1. Hugh Marston Hefner was born on April 9, 1926 to Glenn and Grace Hefner, in Chicago, Illinois.

  2. “I was the best jitter-bugger in the class,” Hef said. He attended Steinmetz High School (class of 1944), where he wrote editorials for the school paper, The Steinmetz Star, and drew cartoons under the alter ego “Goo Heffer.”

  3. Hef majored in psychology at the University of Illinois at Urbana-Champaign, earning his degree in only two and a half years.

  4. Hef married Mildred Williams on June 15, 1949. They divorced 10 years later and had two children together, Christie and David.

  5. During a semester of graduate courses at Northwestern University, Hef wrote a paper called “Sex Behavior in the U.S. Law.” He received an “A” for the research from his professor, marked down to a “B+” for his conclusions.

  6. Hef worked at Esquire as a copywriter for a brief period, but left when he was denied a $5 raise.

  7. In the following weeks, Hef started making plans for a men’s magazine, out of the living room of his South Side apartment.

  8. Hef borrowed $600 from the local bank and loan company and another $8,000 from friends and relatives, from which he was able to put together the first issue of Playboy.

  9. His mother, Grace, loaned him $1,000 to start Playboy.

  10. In early 1953, Hef took a job as the circulation manager of a children’s magazine, Children’s Activities

  11. At night, he worked on the men’s magazine, sending off letters as “Hugh Hefner, Editor in Chief,” or “Hugh Hefner, Advertising Director,” or “Hugh Hefner, Circulation Director.” “It was quite literally a one-man band,” he said.

  12. The magazine was originally called *Stag Party. *

  13. Right before its first issue launched, in September 1953, Hef received a cease and desist letter from a lawyer from Stag magazine because they felt it was an infringement on the title.

  14. After tossing around names like Gentlemen and Sir, the name Playboy was suggested.

  15. Playboy was also the name of a sports car at the time.

  16. The magazine’s logo quickly changed from a stag to a rabbit. “If I wouldn’t have done that, we wouldn’t be here,” Hef said. “It’s very difficult to imagine clubs around the country with girls with antlers on their heads,” Hef said.

  17. In 1953, 70,000 copies of the first issue of Playboy were printed; 52,000 sold.

  18. It launched in November 1953, but there isn’t a publication date on the first issue because Hef wasn’t certain sales would support a second edition.

  19. The first few Playmates of the Month were calendar pictures purchased from a local calendar company.

  20. Once Playboy started shooting the Playmate of the Month, Hef tried to find young women across the country who weren’t necessarily in modeling.

  21. “I wanted to make the statement that beauty was everywhere. So the very notion of the Playmate of the Month was that she was the girl next door,” Hef has said.

  22. Playboy’s first photo shoot was with Charlene Coralis, who worked in the subscription department. Hef renamed her Janet Pilgrim in the magazine.

  23. Hef and Coralis were dating at the time.

  24. In the earliest original Centerfolds, Hef introduced the suggestion of a presence of a man—to insinuate a sexual situation. He is in the background of Janet Pilgrim’s pictorial. “What I was trying to say, quite frankly, was that sex was a natural part of life,” Hef said. “And that nice girls like sex too.”

  25. In 1955, Playboy published a controversial fiction story, “The Crooked Man,” in which homosexuality was the norm.

  26. Gahan Wilson, one of Hef’s favorite cartoonists, first appeared in the magazine in the middle 1950s. His cartoons have run in almost every issue of Playboy since.

  27. In the 1950s, Playboy was turned down by the U.S. Postal Service twice for a second-class mailing permit.

  28. Hef went to Washington D.C. to file a complaint and overturn the mailing ban. He told Writer’s Digest, “Henceforth we will continue to be edited in Chicago, not Washington.”

  29. In 1956, Hef went on The Mike Wallace Interview, his first network appearance after starting the magazine.

  30. After the interview was over, journalist Mike Wallace told Hef, “In five years, you’ll be doing something else.”

  31. Hef thought the magazine would top out at 700,000 subscribers. By its fifth anniversary, it had reached a million—surpassing Esquire.

  32. In the 1950s, many of Hef’s friends were nightclub performers; Sammy Davis, Jr. and Tony Bennett regularly visited Playboy’s Chicago offices.

  33. In October 1959 Hef started taping the late-night variety show Playboy’s Penthouse.

  34. The opening credits showed Hef driving a white Mercedes and smoking a pipe. Hef was living the life he espoused in the magazine, reinventing himself as “Mr. Playboy.”

  35. Playboy’s Penthouse took the subjective perspective of a guest, watching the comedy, conversation and musical numbers in a penthouse apartment.

  36. Hef gave Sammy Davis, Jr. a St. Bernard puppy named “Playboy” when he first appeared on the show.

  37. Tony Bennett is who gave Hef the idea of starting the Playboy Jazz Festival, which still held annually at the Hollywood Bowl.

  38. According to Hef, the hugely successful inaugural event—attracting 20,000 jazz fans to Chicago Stadium in 1959—is what helped turn Playboy into a mainstream brand.

  39. In 1960, at the height of McCarthyism, Hef exchanged letters with Ronald Reagan (then the president of the Screen Actors Guild), who objected to articles in the magazine authored by Dalton Trumbo, one of the blacklisted “Hollywood Ten.”

  40. Hef published a profile of Charlie Chaplin at a time when he was considered the most hated man in America.

  41. Hef’s main reason for buying the Chicago Mansion in 1960 was to have a place to escape to from work. “But very quickly, I brought the work to the Mansion, and from the very early ‘60s on, I was working out of the house,” Hef said. “It’s a way that works very well for me.”

  42. The Chicago Mansion had an underwater bar, accessible by a brass fireman’s pole.

  43. In 1960, Hef opened the first Playboy Club in Chicago.

  44. In a time of segregation, Hef opened his Playboy Clubs up to people of all races.

  45. In 1961, Dick Gregory became the first black comic to perform at the Chicago Playboy Club, opening the door for other black performers in mainstream clubs.

  46. In the September 1962 issue, Alex Haley conducted the first Playboy Interview with Miles Davis. “Miles Davis talked more about race than about music,” Hef said.

  47. Hef wrote the first installment of the Playboy Philosophy for the December 1962 issue, with the notion of doing it for one issue. “It was an editorial in response to our critics,” Hef said. “If I was going to be damned, I wanted to be damned for what I really believed, not what they pretended I believed.”

  48. The Playboy Philosophy ran from December 1962 until January 1966, in 25 installments.

  49. Hef got his lawyer to defend Lenny Bruce when the comedian was arrested in Chicago during a comedy routine in late 1962. He later wrote editorials in the magazine criticizing the injustice of Lenny Bruce’s arrest.

  50. In June 1963, the Chicago police arrested Hef on an obscenity charge, basing it on the Jayne Mansfield pictorial in the June 1963 issue. Hef felt the real reason behind his arrest were his editorials defending Lenny Bruce and criticizing the Chicago police and government. The jury of 11 women and one man deadlocked, and the trial ended in a hung jury.

  51. The June 1963 issue with Jayne Mansfield became Playboy’s biggest seller up to that point.

  52. When the New York Playboy Club opened in December 1962, it didn’t have an entertainment license for a year. But despite having no shows, the club was filled seven days a week.

  53. Playboy published the last piece ever written by Dr. Martin Luther King Jr. in January 1969, “A Testament of Hope”, edited by his widow, Coretta Scott King.

  54. Walking down a Chicago street during the violent clashes between police and protesters at the 1968 Democratic National Convention, Hef was struck across the back with a billy club by a police officer.

  55. Hef’s plane, the Big Bunny, was a stretch version of the DC-9 with overseas capability.

  56. Actor Yul Brynner asked Hef to use the Big Bunny airplane to take Vietnam war orphans, who had arrived in San Francisco, to homes across the country. Playboy Bunnies cared for the infants as they made the cross-country flight.

  57. Hef instituted a special subscription rate for members of the clergy in hopes of encouraging debate.

  58. In 1975, after spending years commuting between Chicago and Los Angeles, Hef made the move to the West Coast. “I have always lived in two cities: My roots come from Chicago, but my dreams came from Hollywood.”

  59. It was ex-girlfriend Barbi Benton who first urged Hef to get a place in Los Angeles.

  60. Hef bought a replica of his star on the Hollywood Walk of Fame and had it installed on the Playboy Mansion grounds.

  61. In response to the government trying to get Playboy removed from convenience stores in the 1980s, Hef ran a “Women of 7-Eleven” pictorial in December 1986. “We figured the best response was satire,” Hef said. “Nothing diffuses censorship like humor.”

  62. In 1985, Hef suffered a stroke, calling it “a stroke of luck,” which he claimed would change the nature and focus of his life.

  63. In 1989, Hef married Playmate of the Year Kimberley Conrad in a lavish ceremony at the Playboy Mansion. They have two kids together, Marston and Cooper Hefner. Cooper is now Chief Creative Office of Playboy Enterprises.

  64. Hef has a genius IQ of 152.

  65. Hef has appeared in Entourage, Sex and the City, Curb Your Enthusiasm, Last Comic Standing and The Simpsons.

  66. Hef’s favorite movie is Casablanca.

  67. Hef’s favorite meal is fried chicken.

  68. Hef has donated more than $1 million himself to help save L.A.’s iconic Hollywood sign, which he considers to be “Hollywood’s Eiffel Tower.”

  69. The Big Bunny was worth more than $5 million, or about $32 million today when adjusted for inflation. It had a disco and slept 16 people.

  70. Despite helping to launch his magazine, Hefner never met Marilyn Monroe.

  71. Hef owns the vault next to Marilyn Monroe’s at Westwood Memorial Park in Los Angeles.

  72. In September 2001, Hef was inducted into the New York Friars Club as an honorary Friar on the occasion of his gala Roast in New York City.

  73. In March 2002, Hef was inducted as an honorary member of the Harvard Lampoon, which named him “Harvard Lampoon’s Best Life-Form In The History Of The Universe.“

  74. Hef hosted Saturday Night Live once, in 1977.

  75. Hef’s personal film archive at the Playboy Mansion in Holmby Hills contains more than a thousand features.

  76. Hef told Esquire in 2007 that he’s "slept with thousands of women—and they all still like me.”

  77. Hef’s favorite nightcap is Jack Daniel’s and Pepsi.

  78. A species of rabbit, the Sylvilagus Palustris Hefneri, is named in Hefner’s honor.

  79. Monday night at the Mansion is known as “Manly Night” when Hef’s closest friends get together for dinner and a movie.

  80. Hef holds the Guinness World Record for owning the world’s largest collection of personal scrapbooks.

  81. Ninety-seven percent of the world’s population have seen the Rabbit Head.

  82. Hef’s daughter, Christie, was CEO of Playboy Enterprises from 1988 to 2008.

  83. Hef enlisted as an infantry clerk in 1944 during World War II.

  84. The first issue of Playboy sold for 50 cents.

  85. Playboy was the first men’s magazine to be printed in braille.

  86. The best-selling issue of Playboy was November 1972, with more than seven million copies sold.

  87. A plaque in front of the original Playboy Mansion in Chicago read, “If You Don’t Swing, Don’t Ring.”

  88. Hef owns more than 200 sets of silk pajamas.

  89. Between its publishing business and clubs, Playboy Enterprises was the largest employer in entertainment for 20 years.

  90. Some of the few men Hef has allowed on the cover of Playboy include Bruno Mars, Seth Rogen, Steve Martin—and Donald Trump.

  91. Hef holds the record as the longest-serving editor-in-chief in magazine history. He still approves every magazine layout—and every Playmate.

Editor’s note: Most of the facts in this list came from Brigitte Berman’s documentary Hugh Hefner: Playboy, Activist and Rebel, but other facts about Hef were included for context, from the Steven Watts biography Mr. Playboy and other Playboy sources.