Top 10 Greatest Regis Philbin Moments

His legacy will last well beyond the final answer. Welcome to WatchMojo, and today we’re counting down our picks for the Top 10 Regis Philbin Moments.

For this list, we’ll be looking at the moments that made Regis one of the most beloved personalities in popular media.

WrestleMania VII
Regis’ interviews always proved entertaining, although few were as eccentric as his ones with WWE Superstars. Professional wrestlers regularly dropped by his talk show and in 1991, Regis served as a celebrity guest at WrestleMania VII. The longtime wrestling fan spoke with several Superstars, but maybe the funniest exchange was between the Undertaker and his manager Paul Bearer. Regis was known for his lively interview style, making him a great comedic foil for two characters who relish in the macabre. Undertaker and Bearer don’t have much to say, ignoring Regis’ questions while measuring him for a casket fitting. Regis does what he can to spark a conversation, but his efforts prove about as effective as trying to get a response out of Bearer’s urn.

“Little Nicky” (2000)
Whenever the cameras were rolling, Regis brought such positive energy to the screen. However, we get to see a darker side of Regis in “Little Nicky,” although his signature optimism is still on full display. As Nicky’s devilish brothers go around possessing people, all hell breaks loose in New York. This evil extends to Regis, who shares what starts off as a lighthearted anecdote. The story takes a grim turn when Regis reveals that he bashed in another man’s head like Robert De Niro in “The Untouchables.” His audience is naturally horrified, prompting an especially appalled reaction from one old lady. Regardless, Regis’ chipper attitude hilariously contrasts his extremely wicked actions. Even when he’s spreading anarchy, Regis is so darn likable.

“The Joey Bishop Show” (1967-69)
Before he was a household name, Regis Philbin was to Joey Bishop what Ed McMahon was to Johnny Carson. But, while “The Joey Bishop Show” was Regis’ first major gig, nothing could compete with “The Tonight Show.” Some of the higher-ups at ABC supposedly felt that Regis was holding Bishop back. Regis walked off the talk show for about a week, but he returned upon receiving encouragement from Bishop and the network. Years later, Regis revealed that his walk-off was part of a publicity stunt that Bishop cooked up in order to draw viewers away from “The Tonight Show.” Regis described this as his most embarrassing TV moment. At least Regis got to take center stage in the talk show’s final episode when Bishop walked off.

“Regis Philbin’s Lifestyles” (1984-87)
There’s no denying that Regis was a good sport; a key example being when he welcomed bodybuilder Samir Bannout onto his show “Lifestyles.” With bulging biceps and a sturdy sixpack, Bannout is undeniably the most athletic person in the room. This doesn’t stop Regis from stripping off his shirt and trying to compete with a Mr. Olympia winner. Flexing alongside Bannout, it’s clear that Regis will have to spend A LOT more time at the gym and the tanning salon if he ever wants to catch up. Even if Bannout is by far the more experienced bodybuilder, you can tell that Regis is having the time of his life. His willingness to poke fun at himself is precisely what made Regis such a wonderful host.

“Live! with Regis and Kelly” (2001-11)
There were times when Regis and Kelly Ripa felt less like co-hosts and more like a comedy duo. One of their best bits took place during Guinness World Record Breaker Week: to break a world record, Kelly must duct tape Regis to a wall in a limited time. Once strapped on, Regis has to remain on the wall for a solid minute. Regis has some snarky words for Kelly as she tapes him up. So, it’s not entirely unwarranted when she stretched a piece of tape across his mouth. Despite Kelly’s best efforts, Regis doesn’t stay suspended on the wall for very long. They might not break the record, but Regis’ nervous expression throughout the ordeal made for a winning segment.

Various
Whereas Regis stood out with an upbeat attitude, comedian Don Rickles was a master of insult humor. Every time the two crossed paths, their opposite personalities made for a pitch-perfect odd couple - and maybe that’s why they were friends for over half a century! There are many examples of their electric chemistry, and as you can expect it doesn’t take long for any encounter to become a comedy routine at Regis’ expense. Rickles pulls no punches; the funnyman generally fires off so many insults per second that Regis can barely get in a word edgewise. Being a good friend of Rickles, though, Regis doesn’t mind being the target of his jabs. If anything, Regis seems happy to play along, almost taking Rickles’ insults as compliments.

“Live! with Regis and Kelly” (2001-11)
Not all of Regis’ interviews were confined to a studio: he often took his act outside. One time, he even hit the streets with Pee-wee Herman, picking up some M&Ms along the way. Also memorable was when he gave Borat a taste of American life. The segment gets off to an appropriately awkward start as Borat feels Regis’ hair and the two hold hands walking down the street. Nevertheless, Regis remains in high spirits throughout and handles the Kazakh journalist better than most, although even he looks uncomfortable after slow dancing with Borat for a little bit. The two inevitably get around to talking about Kelly, which amounts to a clever punchline about how much Regis’ co-host makes per year. The segment closes out with another dance, as Borat refuses to let go of his new American friend.

“How I Met Your Mother” (2005-14)
Regis has made his fair share of classic appearances on sitcoms, notably interviewing Kramer about his coffee table book about coffee tables. Yet, perhaps his most prominent TV cameo was on “How I Met Your Mother.” Regis and Marshall Eriksen have both tasted what they consider to be the best burger in New York. Unable to remember where the burger joint is, the two spend years trying to find it to no avail. Seeing Marshall obsess over a burger is one thing, but seeing Regis become physically violent over it is another level of hilarity. Calling back to his “Joey Bishop” days, Regis walks off a game show when the gang tracks down the burger. There’s a bit of a mixup, but eventually, daddy gets his meat.

“Late Show with David Letterman” (1993-2015)
As a couple of pros in the biz, these two were longtime friends, with “Regis Lee Philbin” making frequent guest appearances on Dave’s shows. One of their most memorable interactions was the time Regis decided to dress as everybody’s favorite green ogre in a surprise appearance. Having previously lent his voice to Mabel the Ugly Stepsister in “Shrek the Third,” Regis and Kelly were hosting the cast of “Shrek The Musical” when Mr. Philbin decided to get dressed up and drop in on his friend. Regis is completely unrecognizable covered under all that green makeup. Having such a distinctive voice, however, Letterman recognizes Regis once he opens his mouth. Given how uncomfortable the costume looks, we understand why Regis doesn’t stick around for long. Even when making a brief walk-on, Regis provides comedy gold.

Before we unveil our final answer, here are a few honorable mentions:

“Take Two with Phineas and Ferb” (2010-11)
As If Regis Couldn’t Be Any *More* Animated

“Hercules” (1998-99)
Regis as Typhon and Kathie Lee as Echidna: A True Power Couple

“Live with Regis and Kathie Lee” (1988-2000)
The First Episode: History in the Making

“Hope & Faith” (2003-06)
Handsome Hal: He’s as Honest as He Is Handsome

“The Morning Show” (1983-88)
The New York Hardcore Interview

“Who Wants to Be a Millionaire” (1999-)
While the name Regis Philbin will always be tied to talk shows, he was equally a giant in the game show world, having been both a host and a celebrity contestant throughout his career. As far as game shows go, though, Regis will forever be remembered for his time on “Who Wants to Be a Millionaire.” It’s impossible to single out his best “Millionaire” moment, whether it was the first time he coined his iconic catchphrase or his ecstatic reaction the first time a player won the million dollars. But not only was Regis an iconic “Millionaire” host; he also sat in the hot seat himself: revisiting the show during Meredith Vieira’s tenure, Regis was asked a question that seemed tailor-made for him. Strangely enough, he got the answer wrong at first! Regis would answer correctly on his second try, but not before Vieira had a little fun with him.