7 ‘Hollywood Squares’ Iterations, From Its 1966 Debut to the New ‘Celebrity Squares’

DC Young Fly hosting 'Celebrity Squares'
VH1

Time to tune your television to the latest Tinseltown take on tic-tac-toe. Celebrity Squares, a new spin on the classic game show Hollywood Squares, hits VH1 on Tuesday, October 17, at 8/7c, with comedian DC Young Fly hosting.

“This show offers a fresh interpretation of the iconic Hollywood Squares format, with a focus on celebrating Black pop culture,” Tiffany Lea Williams, EVP of unscripted programming and development at BET, explained in a press release. “With DC Young Fly’s laugh-out-loud humor, it promises to deliver a fun and exhilarating viewing experience.”

And now, with the introduction of Celebrity Squares, the Hollywood Squares format has aired during every decade since the 1960s. Check out a timeline of the original Hollywood Squares and its successors in the photo gallery below.

Celebrity Squares, Series Premiere, Tuesday, October 17, 8/7c, VH1

Paul Lynde, Rosie Marie, Peter Marshall, and Cliff Arquette of 'Hollywood Squares'
Everett Collection

NBC’s Hollywood Squares (1966–1980)

After a 1965 pilot, the daytime NBC version of Hollywood Squares began in earnest in 1966, with Peter Marshall (second from right) as host and (from left to right) Paul Lynde, Rose Marie, and Cliff Arquette as regular panelists.

“I thought it was going to be a 13-week gig,” Marshall reflected in a 2022 interview with Closer Weekly. “In the beginning, we were up against The Dick Van Dyke Show reruns. We languished for maybe nine months. And then all of a sudden, we started growing. The next thing you know, we were a big hit.”

Ted Cassidy with chimp on 'Storybook Squares'
Everett Collection

NBC’s Storybook Squares (1969)

For this children’s spinoff, celebrity panelists — including many from the original series — dressed up as characters and joined Marshall on a castle-themed set, while pint-sized players competed for age-appropriate prizes. In one episode, for instance, Charo played Lady Godiva, Roddy McDowall played Pinocchio, and Joan Rivers played the Old Woman Who Lived in a Shoe, while William Shatner appeared as his Star Trek character, Captain Kirk. (Pictured here is Ted Cassidy dressed as Tarzan, with Cheetah the chimp at his side.)

“It was just about the most fun I ever had doing television,” Marshall tweeted in 2021. “Almost everybody (but Paul Lynde) loved it.”

Jon 'Bowser' Bauman and Gene Rayburn on 'Match Game-Hollywood Squares Hour'
NBC/Courtesy: Everett Collection

NBC’s Match Game-Hollywood Squares Hour (1983–1984)

For one season of NBC’s daytime programming, the network combined Match Game and Hollywood Squares for an hour-long game show, with celebrity panelists pulling double duty. Gene Rayburn hosted the first half, reprising his role as Match Game host, and Sha Na Na singer Jon “Bowser” Bauman hosted the second, taking on the Hollywood Squares format.

The game show couldn’t compete with the ratings of ABC’s General Hospital and CBSGuiding Light, per The Encyclopedia of Daytime Television. But it does have at least one claim to fame, Bauman tweeted in 2019. “Understand that this was the only completely honest version of [Hollywood] Squares ever, where no Squares were sitting there with the punch lines of the jokes in front of them,” he wrote.

Whoopi Goldberg and Tom Bergeron of 'Hollywood Squares'
King World Prod./Courtesy: Everett Collection

Syndicated Hollywood Squares (1971–1981, 1986–1989, 1998-2004)

Hollywood Squares aired in syndication from 1971 to 1981 with Marshall returning as host and then again from 1986 to 1989 with John Davidson taking over the emcee job.

“It’s a proven formula, Hollywood Squares. You’ve got nine stars, so you’ve got to like somebody!” Davidson told That Thing They Did this year. “And it’s very entertaining. … I never met so many people in the business. It was like a big Hollywood party.”

Another syndicated version (pictured here) aired from 1998 to 2004, with Tom Bergeron hosting and Whoopi Goldberg executive producing, residing in the center square, and getting A-list talent like Billy Crystal, Cindy Crawford, Antonio Banderas, and Robin Williams to be panelists.

“They’re people you’ve never seen on shows like this before,” Bergeron told the Orlando Sentinel in 2000. “They come, and they come regularly. It’s Whoopi, it’s her cachet that she’s put on the line. I just have the greatest respect for her. I marvel at what she’s done with her career, and how she’s not afraid to take chances. This show was a risky move for someone in her position.”

DeRay Davis hosting 'Hip Hop Squares' with DeRay Davis and
MTV/Courtesy: Everett Collection

MTV2 & VH1’s Hip Hop Squares (2012, 2017–2019)

A hip hop-themed version of Hollywood Squares hit MTV2 in 2012, with Hot 97 radio deejay Peter Rosenberg hosting. MTV brought in producers from the Bergeron version of Hollywood Squares but mixed up the format with an in-house DJ and cocktail waitresses on set. “We wanted it to feel a little bit unpredictable, a little bit bumpy,” MTV2 senior vice president Paul Ricci told The New York Times.

Hip Hop Squares made a comeback on VH1 in 2017 and aired until 2019. That time around, DeRay Davis (pictured here) hosted, while rapper Ice Cube exec-produced. “It’s great to have guys from the hip hop and just pop world up there having a ball,” Ice Cube told CBS This Morning in 2017. “A lot of them didn’t know how to play tic-tac-toe, so it was extra fun to see them kind of stumble around.”

Bob Saget hosting 'Nashville Squares'
CMT

CMT’s Nashville Squares (2019)

When CMT introduced a country-music version of the game show in 2019, Nashville stars like Tanya Tucker, Mickey Guyton, and Deana Carter sat in the squares. And producers — including Hip Hop Squares alum Jesse Collins — tapped Bob Saget as host.

“I thought, ‘Why me?’ Is Jeff Foxworthy or Bill Engvall not available? They said, ‘No, we just think you know how to do this,’” Saget told TV Insider at the time, adding that he was going to perform his own country song, the vegan-themed “Corn’s My Meat,” on Nashville Squares. “It’s a silly reboot of the show. I just had a blast doing it.”

'Celebrity Squares'
VH1

VH1’s Celebrity Squares (2023)

Celebrity Squares, another iteration with Collins as EP, premieres on October 17 with Kevin Hart on the producing team and DC Young Fly at the podium. “I was on Hip Hop Squares prior to this when DeRay Davis was the host, and I kinda got the glimpse and kinda got the energy,” Young Fly told Fox 5 Atlanta. “Once they called me — and salute to Kevin Hart and Jesse Collins and [showrunner] Nile Evans — they was like, ‘You know what, we want a younger host, we want to try to revamp the show.’ … It’s one of the shows where the older generation and the younger generation can watch it together.”