The Films of Hugh Hefner

When we say "The Films of Hugh Hefner," we're not necessarily talking about his roles in motion pictures. Oh, Mr. Hefner, who passed away at the age of 91 on September 27, 2017, certainly appeared in a number of films and guest-starred in several TV series. We will get to those eventually, but there was a period of time, specifically the decade from 1971 to 1980, when the tireless entrepreneur dabbled as a movie producer...and we're not talking about producing countless Playboy Playmate and centerfold videos like "Jessica Hahn Bares It All."

We first must introduce another high-rolling entrepreneur named Victor Aubrey Lownes III, born 1928 in Buffalo, New York, to wealthy parents who were tapped into the fortune from the Yale lock company. After accidentally shooting and killing a best friend at the age of 12, Victor was shuttled off to a military junior college in New Mexico, where he befriended Nicky Hilton, son of the prosperous hotelier Conrad Hilton.

Fast-forward past college at the University of Chicago with an MBA, a marriage at age 18, a burgeoning career as a manager at Yale Lock Manufacturing, with two children, and you would have found Lownes experiencing a midlife crisis at the age of 26, who then decides to abandon his family. He moved to Chicago and met Hugh Hefner, whose first edition of Playboy magazine hit the newsstands in December 1953, at a party in 1954. After writing articles for the publication, Lownes was brought on-board as a full-time promotions director. As a vice president for the company, he became a close confidant of Hefner while gaining a reputation for dating Playboy Playmates.

Lownes is credited with initially coming up with the concept of Playboy Clubs in the U.S. His girlfriend at the time suggested to Hugh Hefner the idea of dressing the clubs' hostesses in a version of the tuxedoed Playboy Bunny character. At first, Hefner was reluctant, as he had always viewed the rabbit as a male.

By the mid-1960s, Victor Lownes was running Playboy Europe and the United Kingdom Playboy Clubs. Between the first and second season of the BBC comedy sketch series "Monty Python's Flying Circus," Lownes convinced the troupe of five British comedians and an American animator (Minneapolis-born cartoonist Terry Gilliam) that a feature film would be the ideal way to introduce their iconoclastic humor to the U.S. market. With Lownes as executive producer, "And Now for Something Completely Different" was distributed by Hefner's Playboy Productions.

The troupe's quintessential "Lumberjack Song" - "I cut down trees,
I skip and jump / I like to press wild flowers / I put on women's
clothing / And hang around in bars" - as performed by Michael Palin
and Carol Cleveland, gets the big-screen makeover on-location
in "And Now for Something Completely Different."

The Pythons soon grew to resent Lownes' increasing interference during production. Terry Jones and Michael Palin later complained that the final film, which included 46 sketches and segments, played out as "nothing more than jokes behind desks."

Michael Palin and John Cleese recreate the Pythons' memorable
"Dead Parrot" sketch ("This is an EX- parrot!") in "And Now for
 Something Completely Different." The sets for the film were built in
an abandoned dairy rather than onmore expensive studio sound stages

The movie initially had little success on American screens but fared better, especially on college campuses, in a 1974 re-release. Not at all coincidentally, "Monty Python's Flying Circus," which originally aired on BBC television from 1969 to 1974, made an inauspicious debut in the U.S. in 1974 on a PBS affiliate in Dallas, and quickly gained steam on public television stations across America.

In August of 1969, Victor Lownes was partying in London with filmmaker Roman Polanski, who had recently directed the classic horror picture "Rosemary's Baby," when Roman's pregnant wife of 19 months, actress Sharon Tate, and four friends were brutally murder by members of the Manson "family" in Los Angeles.

In 1967, before they were married, Tate had costarred with Polanski in the director's dark comedy "The Fearless Vampire Killers." A photographer in his own right, Roman took pictures of Sharon on the set of the movie for a pictorial in Hefner's Playboy magazine (pictured below).

Presumptuously, the text for the photo spread declares,
"This is the year Sharon Tate happens."

Some time after encountering Roman Polanski at the party, Victor Lownes persuaded Hugh Hefner to provide $1.5 million to help finance Polanski's planned production of "Macbeth," Shakespeare's tragedy of the murderous ambition of a Scottish lord and his wife and their undoing by guilt and madness as the bodies of their victims pile up.

The play had been notably adapted for the screen in 1948 by producer-director Orson Welles, who starred as Macbeth, but in 1971, no major movie studio would touch it. Interestingly, the play itself is the subject of a long-held superstition that discourages mention of the name "Macbeth" inside a theater unless in the actual staging or in rehearsal. To avoid misfortune, performers refer to it as the "Scottish Play" and Macbeth himself as the "Scottish King." The curse allegedly stems from a belief that Shakespeare used the spells of real witches in the play's text, which angered the sorceresses and caused them to curse the play.

Perhaps inspired by director Franco Zeffirelli's buoyant resuscitation of Shakespeare's "Romeo and Juliet" in 1968, which cast youthful newcomers Leonard Whiting (age 17) and Olivia Hussey (15) as the breathless lovers (pictured above), Polanski sought out young, good-looking actors to portray Macbeth and Lady Macbeth.

Twenty-nine year-old Jon Finch, cast as Macbeth, had appeared in small roles in the Hammer Film Productions "The Vampire Lovers" and "The Horror of Frankenstein," while Francesca Annis, age 26, cast as Lady Macbeth, began acting professionally in her teens.

One might say that in a certain light, "Macbeth's" Francesca Annis
(top) bore a striking resemblance to the late Sharon Tate (bottom).

The budget had been set at $2.4 million, but Polanski, shooting at historic locations in Northumberland and Wales, was $600,000 over-budget when he mocked Playboy's "generosity," creating a fallout between Polanski and Lownes. Financial backers wanted Polanski fired. Director Peter Collinson (best known for the original "The Italian Job") filmed additional scenes at England's Shepperton Studios. Polanski subsequently agreed to give up a third of his salary, while Hugh Hefner pitched in another $500,000 to complete the film.

In his autobiography, Polanski stated he wanted to be true to the violent nature of Shakespeare's work, although he was aware that his first project after Sharon Tate's murder would draw closer scrutiny than if he had made a comedy, in which case he believed he would be deemed callous.

"Macbeth" culled mixed reviews, most of which directed negative criticism at its explicit violence and gore, especially in light of the Manson killings, as well as its inclusion of nudity. In one scene, adapted by Polanski and co-screenwriter Kenneth Tynan (a British theater critic Polanski respected for his encyclopedic knowledge of Shakespeare), Lady Macbeth delivered her sleepwalking soliloquy in the nude.

Many believed the nude scene was a concession to the movie's financial benefactor, Playboy Productions, however, Polanski said the screenplay was written before Hefner's involvement. And anyway, according to Polanski and Tynan, people in that era and place slept naked.

Hugh Hefner, Francesca Annis, and Roman Polanski
put on brave faces at the after-party for the premiere.

The film was a box office bomb. Initially, Playboy estimated it lost $1.8 million, while the losses, in fact, amounted to $3.5 million. The chasmic deficit caused future Shakespeare film projects to be red-flagged as commercial risks until director-star Kenneth Branagh's breathtaking jump-start of Shakespeare's "HenryV" in 1989.

In 1974, Victor Lownes married 1973 Playboy Playmate of the year, Marilyn Cole, 21 years younger, who held some esteem as the magazine's first full-fontal nude centerfold (pictured above).

In 1981, Lownes (pictured above, with wife Marilyn Cole) envisioned opening a Playboy casino in Atlantic City when he was accused of irregularities by the Gaming Board for Great Britain. Hefner panicked and promptly fired Lownes. Lownes eventually reconciled with Roman Polanski, while he suffered little more than wounded pride in his relationship with Hefner, with whom he remained good friends personally. Rarely seen in public in his later years, Lownes died in January 2017 at the age of 88.

Marilyn Cole poses with Hugh Hefner and husband Victor Lownes.

Undaunted as a movie producer, High Hefner next set his sights on the 1973 film adaptation of the best-selling 1967 book The Naked Ape. Published during a phase that produced a number of pop non-fiction works such as Everything You Always Wanted to Know About Sex* (*But were Afraid to Ask), Future Shock, and Chariots of the Gods? the mod-anthropology book described humans much as zoologists describe animals. The author, Desmond Morris, is, in fact, a zoologist and ethologist who worked as a curator of mammals at the London Zoo, specializing in primates. His particular take on the nature of humans is that our species is best perceived as a very complicated primate. Understandably, the book made for popular reading because it focused on sex and mating rituals.

"The Naked Ape," the only film made by Broadway director and Tony Award nominee Donald Driver, was a combination of live actors and animation. The flesh-and-blood cast featured Johnny Crawford, best known as Mark McCain, the wide-eyed son of Chuck Connors in the early 1960s TV series "The Rifleman," now cast as a randy (and, at 27, overage) college student, and 23-year-old Victoria Principal, fresh from her auspicious debut as Maria opposite Paul Newman in director John Huston's "The Life and Times of Judge Roy Bean" (which garnered her a Golden Globe Award nomination as Most Promising Newcomer).

Victoria Principal, Johnny Crawford, and TV actor Dennis Olivieri
wait in line at a college bookstore in "The Naked Ape."

Tony Mastroianni of the Cleveland Press noted, "Take a non-book, base a movie on it and the result is a non-movie." He called it "the kind of film made for classroom use by such outfits as Encyclopedia Britannica" but imagined by Playboy. "The movie deals mainly with the areas of sex and aggression. No matter how hard they try, the moviemakers have been unable to mix anthropological information and speculation with entertainment...The quality of filming and acting throughout is of the kind used in slick television commercials."

The book was so named because of the 193 species of apes
and monkeys, only humans are not covered in hair.

To quote one internet reviewer, "The oddest thing about it is that it's all presented in a remarkably tame PG format, which is surprising when one considers that it's a movie by Hugh Hefner from a book about primitive sexual urges!"

For a time, Hugh Hefner turned his attention to producing made-for-television movies, including 1973's "The Third Girl from the Left," a sudsy soap opera starring Kim Novak as an aging chorus girl and Tony Curtis as a nightclub entertainer (pictured above).

"The Third Girl from the Left" features Hefner's girlfriend
at the time, Barbi Benton, in a supporting role.

Among Hefner's other TV projects was the 1981 eco-drama "A Whale for the Killing," filmed in Newfoundland and Labrador and featuring Peter Strauss ("Rich Man, Poor Man"), Dee Wallace ("The Howling," "Cujo"), and Richard Widmark.

The 1974 theatrical release "The Crazy World of Julius Vrooder," executive produced by Hugh Hefner, starred Timothy Bottoms (best known for his star-making performances in "The Last Picture Show" and "The Paper Chase") as a Vietnam War veteran who feigns insanity, then escapes from the VA hospital into an underground tunnel and builds a booby-trapped hideaway under a highway ramp. Barbara Hershey plays the nurse with whom Bottoms falls in love.

The movie was made during the downside of Barbara's career, when she established a reputation as a "hippie." During a six-year relationship with actor David Carradine, she changed her last name to Seagull, as a tribute to a bird accidentally killed during the production of her 1969 film "Last Summer." When she billed herself as Barbara Seagull in "the Crazy World of Julius Vrooder," Hugh Hefner insisted her $50,000 paycheck be cut in half since the new name reduced her box-office draw. "You're paid for your name," Timothy Bottoms said years later, "the name is everything."

In her review for The New York Times, Nora Sayre said the movie "drowns its antiwar theme in a cataract of cuteness." Calling Timothy Bottoms a "beguiling" actor, Sayre noted "here he has been directed to be elfin...he seems in peril of turning into Peter Pan." The supporting cast included Albert Salmi, Lawrence Pressman, Richard Dysart, Debralee Scott, and Otis Day (of Otis Day and The Knights fame in "National Lampoon's Animal House"). The film also featured a rare acting turn (not to mention his final piece of work in motion pictures) by veteran Hollywood director George Marshall, whose venerable career began in silent films in 1916 and included movies with Laurel and Hardy, W.C. Fields, and Bob Hope.

Some reviewers thought George Marshall's performance as a
World War I vet named Corky was worthy of an Oscar nomination.

In 1979, executive producer Hugh Hefner collaborated with co-producer and independent movie mogul Roger Corman on the Peter Bogdanovich venture "Saint Jack," starring Ben Gazzara in a tour de force performance as an errant American in Singapore during the Vietnam War era. Probably best known for his villainous roles as a crooked town boss in "Road House" and as a pornographer and loan shark in "The Big Lebowski," Gazzara seemingly channels the spirits of such earlier Hollywood solders of fortune as Humphrey Bogart and Alan Ladd as an expatriate who freelances as a pimp and dreams of opening an opulent brothel until he runs afoul of the local triad gangs. As a cynic attempting to, in the words of one critic, "forge a reasonably honorable life in a dishonorable profession," he delivers a memorable, complex character study.

Pictured here alongside Ben Gazzara, the effortlessly versatile
character actor Denholm Elliott portrays an affable British
businessman with a bad ticker and a wistful pipe dream to retire
in a Georgian house in the west of England.

The film contains a cameo by George Lazenby (best known for his one-and-only shot as 007 in "On Her Majesty's Secret Service") as a visiting U.S. senator whom Gazzara is hired to photograph in a rendezvous with a young male prostitute, providing Gazzara with a conscience-defining crisis. In an icy, quirky turn, director Bogdanovich himself appears as the Cuban cigar-smoking mobster who wants the compromising photos.

Peter Bogdanovich. Nina Bagharib, George Lazenby,
and Ben Gazzara share an elevator in "Saint Jack."

This was Peter Bogdanovich's first film in three years, following a string of movies designed to showcase his various mistresses - Cybill Shepherd in "Daisy Miller" and "At Long Last Love," Jane Hitchcock in "Nickelodeon" - all box-office disasters. In a 2006 interview with The New York Times, Bogdanovich lamented that "Saint Jack" and its follow-up, 1981's "They All Laughed," a romantic comedy about lovelorn private detectives in New York City with an ensemble cast featuring Ben Gazzara, Audrey Hepburn, John Ritter, Patti Hansen, and Dorothy Stratten, were two of his best films "but never received the kind of distribution they should have."

"Saint Jack" producer Roger Corman had given Bogdanovich an early crack at directing some scenes in 1966's "The Wild Angels," starring Peter Fonda, Nancy Sinatra, and Bruce Dern, while executive producer Hugh Hefner's participation might explain the movie's otherwise unnecessary steamier scenes, not to mention, of course, the obligatory accompanying pictorial in Playboy magazine.

In April of 1964, Peter Sellers became the first man to pose for the cover of Playboy magazine.

The chameleonic actor had recently essayed the trio of roles as a British RAF group captain, the milquetoast U.S. president, and the crippled, former Nazi scientist in director Stanley Kubrick's savage political satire "Dr. Strangelove," and the magazine's pictorial depicted him lampooning various vintage Hollywood scenarios, such as "Dracula."

In what proved to be his final film, 1980's "The Fiendish Plot of Dr. Fu Manchu," executive produced by Hugh Hefner, Peter Sellers played the dual roles of the evil 168-year-old Chinese supervillain and his archenemy, retired Scotland Yard commissioner Nayland Smith, in what was intended as a bizarre farce like Sellers' old Goon Show radio comedy program.

(Top) Peter Sellers as Fu Manchu and (bottom) as Nayland Smith,
is joined by the incomparable Helen Mirren
as police constable Alice Rage.

Sellers fired original director Richard Quine (who had recently directed Peter in the comedic swashbuckler "The Prisoner of Zenda") and replaced him with John G. Avildsen (who won a directing Oscar for "Rocky"). Avildsen soon parted company with Sellers and was replaced by Piers Haggard, a British director who had made the original BBC production of "Pennies from Heaven." Sellers eventually dismissed Haggard and assumed the directing chores himself.

Sellers takes over behind the camera with Helen Mirren at his side.

"Nobody sets out to make a bad movie," Roger Ebert observed in his review of "The Fiendish Plot of Dr. Fu Manchu," "but bad movies are made, and the people making them often suspect the worst, even at the time. But they have to forge ahead."

"The Fiendish Plot of Dr. Fu Manchu," for all intents and purposes, ended Hugh Hefner's dabbling in feature films. Beginning in the late 1990s, he started producing handsomely mounted documentaries about such former luminaries as Mary Pickford, Theda Bara, Louise Brooks, Clara Bow, Marion Davies, and Rita Hayworth, narrated by the likes of Charlize Theron, Shirley MacLaine, Kim Basinger, Uma Thurman, Rosanna Arquette, Whoopi Goldberg, and Courtney Love. Diane Lane narrated the 2007 documentary "Why Be Good? Sexuality & Censorship in Early Hollywood," and Kenneth Branagh narrated "Lon Chaney: A Thousand Faces."

As mentioned at the onset, Hugh Hefner made a number of appearances in film and on television, but invariably he played himself, or a fictional representation of his persona, as the wealthy publisher of the world's leading men's magazine. For instance, his first acting role was as the Bunny Club Manager in a 1965 episode of the cop series "Burke's Law," starring Gene Barry as the millionaire captain of the Los Angeles Police homicide division.

LAPD Captain Amos Burke (Gene Barry) has an eyeful
at the anonymous "Bunny Club" in "Burke's Law."

In 1968, Hefner appeared on "Rowan & Martin's Laugh-In," playing off Ruth Buzzi's recurring character of spinster Gladys Ormphby (pictured below, with Dan Rowan).

After Barbi Benton, Hef's main squeeze at the time, joined the cast of "Hee Haw" in its third season, Hugh felt obligated to make at least one cameo appearance on the countrified version of "Laugh-In."

Hugh Hefner, confronting Barbi Benton, does not appear at all
comfortable in his bib overalls wardrobe for "Hee Haw."

On a 1969 episode of "Get Smart" titled "The Treasure of C. Errol Madre" (in which the spy comedy spoofed the classic film "The Treasure of the Sierra Madre"), Hefner, an old friend of series star Don Adams, had a cameo role as one of the CONTROL agents jammed into an elevator that is being used as the Chief's new office due to cost cutting.

Hugh Hefner (far left) appears in "Get Smart."

Hefner had a memorable cameo - as himself, no less - in a 1982 episode of "Laverne & Shirley" appropriately called "The Playboy Show," guest-starring Carrie Fisher (pictured below).

It's difficult to dismiss Carrie's discomfiture in her bunny costume.

Hugh Hefner became a familiar face on a number of sitcoms and drama series from the 1970s into the 2000s, including "The Odd Couple," "Blossom," "The Larry Sanders Show," "Roseanne," "V.I.P.",  "Sex and the City" (of course), "Las Vegas," "The Bernie Mac Show," "Entourage," and "Curb Your Enthusiasm" (pictured below).

Possibly Hefner's oddest television cameos were guest appearances on the professional wrestling show "WWE Raw" in 1999 and 2000. He's pictured here alongside the late Chyna. Wrestler, bodybuilder, glamor model, and pornographic movie star ("She Hulk XXX"), Chyna, who was billed early in her wrestling career as the "Ninth Wonder of the World," died in April 2016 from an "accidental" overdose of alcohol, anxiety drugs, painkillers and sleeping aids. She was 46.

In 1993, Hugh Hefner provided the voice for his guest role on the Fox animated series "The Simpsons," a function he repeated on a 2007 episode of "Family Guy."

On the big screen, Hefner made his feature film debut as a toga-clad entrepreneur in the Roman Empire segment of Mel Brooks' 1981 comedy "History of the World Part I." As narrator Orson Wlles extols Rome as the "vortex of modern civilization" and the "fountainhead of culture," the camera moves through the crowded Forum, past a V and X cent store, soothsayers, column salesmen, a used chariot lot, and a banner advertising an annual orgy and buffet ("First Served First Come"), before finally settling on Hugh, dressed in a toga, clutching his ever-present pipe, and surrounded, of course, by a bevy of beauties.

"I'm very excited about it," Hefner tells his comely listeners.
"It's a new concept. It's called a centerfold."

The palatial Playboy Mansion in Holmby Hills made its motion picture debut in 1987's "Beverly Hills Cop II," with Eddie Murphy reprising his role as transplanted Detroit detective Axel Foley. Hefner made a brief appearance, accompanied by his current girlfriend, Carrie Leigh (pictured below).

Not unlike the Playboy Mansion, "Beverly Hills Cop II" provided fledgling standup comic Chris Rock with his first film role, as a valet at the Mansion (pictured below).

Hefner attended the premiere of "Beverly Hills Cop II" on the arm of Miss Leigh (pictured below), who had been proclaimed "The First Lady of the Playboy Mansion" on the July 1986 cover of Playboy magazine. By early 1988, Carrie was asking for several million dollars in a palimony suit against Hugh. She eventually found wedded bliss elsewhere and dropped the suit.

Carrie Leigh was Miss Bikini Ontario 1982.

Hugh Hefner's final two feature films were 2008's "The House Bunny" and 2009's "Miss March," both appearing, naturally, as himself. Anna Faris, the talented comedic actress who has starred in the CBS sitcom "Mom" since 2013, plays the title role in "The House Bunny," a Playboy Bunny ousted from the Playboy Mansion at age 27 ("59 in Bunny years"), who finds a renewed purpose in life as the house mother of the kind of sorority of misfits typically on display in any frat/sorority house comedy since "Animal House."

Hugh Hefner made Anna Faris an honorary Playboy Bunny, gifting
her with a Bunny necklace, which she wore in the film, as pictured
above, with "The House Bunny" costar Emma Stone.

Directed by Fred Wolf, a former standup comic and writer for "Saturday Night Live" whose screenplays include "Black Sheep," "Joe Dirt," and "Grown-Ups," from a script by the writing team of Karen McCullah and Kirsten Smith ("10 Things I Hate About You," "Legally Blonde," "Ella Enchanted"), "The House Bunny" provided Anna Faris with a solid supporting cast, including Colin Hanks (Tom Hanks' eldest son), Emma Stone (Oscar-winning Best Actress for 2016's "La La Land"), Kat Dennings (costar of TV's "2 Broke Girls"), Beverly D'Angelo (best known as Ellen Griswold in the "National Lampoon Vacation" comedies), and Rumer Willis (eldest daughter of actors Bruce Willis and Demi Moore). Writers McCullah and Smith, along with Faris, were also among the producers of the film for Adam Sandler's Happy Madison Productions.

Hef, along with three of his interchangeable threesome of blonde
companions, makes an obligatory cameo in "The House Bunny."

"Miss March" (2009) was written by, directed by, and starred Trevor Moore and Zach Cregger, two members of the IFC sketch comedy troupe "The Whitest Kids U' Know." As succinctly summarized by the International Movie Database, "A young man (Cregger) awakens from a four-year coma to hear that his once-virginal high school sweetheart has since become a centerfold..." Cregger and "his sex-crazed best friend (Moore)...take a cross-country road trip in order to crash a party at the magazine's legendary mansion headquarters and win back the girl."

"Miss March" was summarily and universally dismissed as the unequivocal worst movie of the year. Salon's website critic called it "the biggest pile of crap I've seen in ages," Variety's John Anderson dubbed it "excremental," while Melissa Anderson of L.A. Weekly said it "sprays like an exploding colostomy bag for 89 minutes."

Trevor Moore (left) and Zach Cregger join the Pajama Man
in the Playboy Mansion.

Robert Wagner (best known these days as Dr. Evil's Number 2 in the "Austin Powers" films) was originally cast as Hugh Hefner, but test screening audiences, who were already familiar with Hefner from the E! series "The Girls Next Door," failed to connect with Wagner. Fortunately for Cregger and Moore, Hugh liked the script and agreed to take part. Hefner also managed to work in a role for 2007
Playmate of the Year Sara Jean Underwood (pictured below, with Cregger and Moore).

Coincidentally, Sara Jean Underwood portrayed a Playboy Playmate in "The House Bunny," and incidentally, Hefner's performance in "Miss March" garnered a Golden Raspberry Award nomination for Worst Supporting Actor (Billy Ray Cyrus won for his role in his daughter Miley Cyrus' "Hannah Montana: The Movie").

Both "House Bunny" and "Miss March" were co-produced by Jason Burns, who was then senior vice president of the mainstream production company for Playboy Enterprises.

Admittedly, in his later years, Hugh Hefner had become, more or less, a self-parody. For instance, here's a picture from 1970 of Hugh and Barbi Benton, who was undoubtedly the most popular if not most recognizable among Hef's long, long line of girlfriends. Compare that Hefner with the one in the photo below, reuniting with Benton in 2005.

Long before he poked fun at himself in "The House Bunny" and "Miss March," he played himself as the host of a couple of syndicated variety-talk shows: "Playboy's Penthouse," which aired from 1959 to 1961, and "Playboy After Dark," broadcast from 1969 to 1970. Part of the charm of both programs was Hefner's awkwardly forced casualness as the host of manufactured cocktail parties, featuring comedians and musicians from various genres in an attempt to spread the magazine's philosophy beyond the printed page and to let readers and non-readers of the publication get to know Hefner.

"Playboy's Penthouse" was recorded at the TV station WBKB in Chicago, on a set designed to look like Hefner's own swanky apartment, with Playboy Playmates and Bunnies mingling with the guests. Hugh's first guest was controversial standup comic Lenny Bruce (pictured below).

"This is kind of an interesting party," Lenny Bruce told Hefner. "I first figured it would be like sort of a TV typical fake party, but it's got a good party feel to it, with some pretty chicks..." Hefner said, "Well, we have the girls and we serve real liquor...It does the trick."

Other guests in the "Penthouse" included Nat King Cole, Bob Newhart, Ella Fitzgerald, Sammy Davis Jr., and Buddy Rich.

The then-ubiquitous Barbi Benton cohosted "Playboy After Dark."

The first season of the revamped "Playboy After Dark" in 1970 was videotaped at CBS Television City in Los Angeles, the second season was taped at KTLA Studios on Sunset Boulevard in Hollywood. Hefner wanted the Chicago Playboy Club-inspired set to resemble a converted firehouse. Midway into production, Hefner decided the set should reflect a theme for each taping, such as the Roaring '20s or "Hawaiian Night," with party guests and extras appropriately costumed.

Jerry Lewis and Sammy Davis Jr. entertain a captive gathering,
including Hugh Hefner and singer-actor Anthony Newley
(far right) on "Playboy After Dark."

Comedians who appeared on "After Dark" included Hefner's longtime pal Don Adams, as well as Shelley Berman, Joey Bishop, Sid Caesar, Professor Irwin Corey, Bill Cosby (who - surprise! - became a fixture at the Playboy Mansion), Rich Little, Louis Nye, and Mort Sahl.

Host Hugh Hefner keeps a watchful eye out for Roman Polanski
while chatting with the lovely Sharon Tate.

Like its predecessor, "Playboy's Penthouse," "Playboy After Dark" was noteworthy for its remarkable diversity, particularly in its vast array of musical guests, which ran the gamut from jazz to R&B, folk, rock and country.

On a January 1969 broadcast of "Playboy After Dark," Jerry Garcia
shares a laugh with Playmate/Bunny Dolly Read. Grateful Dead
performed "Mountains of the Moon" and "St. Stephen." (Dolly Read,
who starred in Russ Meyer's "Beyond the Valley of the Dolls," was
the future wife of "Laugh-In" cohost Dick Martin.)

The incident might be apocryphal, but on a May 2015 airing of "Conan," as Grateful Dead drummer Bill Kreutzmann told O'Brien, the band's sound engineer, Bear (real name Owsley Stanley, who also happened to be a clandestine chemist and the first individual to manufacture massive amounts of the hallucinogen LSD), dosed the TV crew's coffee pot with acid. There were no dire consequences, only confused cameramen and a seemingly petrified Hugh Hefner.