The Most Popular Las Vegas Entertainers of All Time

The history of Sin City is steeped in wild tales of reckless abandon, set to the greatest soundtrack in history. The following chronicle is a testament to the endless stream of creative talent flowing through Las Vegas, from its mobster beginnings to the modern megaresort era. And the popularity of an entertainer is not measured merely in millions; some of them have carved their names in history as Las Vegas icons. These are the most popular Las Vegas entertainers of all time.

The Desert Oasis

Before the Las Vegas Strip earned its 1970s reputation as the place where entertainers go to fade away into obscurity, there was an explosion in quality talent playing the Strip. During the 1950s, Vegas experienced a major expansion period, which resulted in new hotel casino opening up practically every few months. Nonstop construction was overseen by an unlikely mix of legitimate hoteliers and retiring mobsters from the East Coast.

As new hotel casinos opened, they needed to attract customers to compete with every other flashing light on the Strip. The jingling and jangling of the real money slot machine games weren’t enough to draw the crowds, so the owners turned to a different type of music: they hired top entertainers to fill their stages. And in the true spirit of competition, each casino tried to hire more prominent stars than the next. Soon came higher pay and longer engagements for the talent. And Las Vegas entertainers with the biggest names on the marquis were called the headliners.

The Headliners

Back in the early days of the entertainment industry, the lion’s share of the profits went to the fat cat promoters. Film stars and musicians worked for peanuts by today’s standards, some of them only earning a few hundred dollars per week. Even adjusted for inflation, they got paid crap. But the Vegas mobsters and their entourage loved the performers they hired, and gave them massive amounts of money to play, and even stay. Whether it was the result of mobster machismo or hotelier hubris did not matter; the new wave of Vegas entertainers got paid to play.

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One of the first of the big name Vegas headliners was Nat King Cole, who played on the opening night of the Thunderbird Hotel in 1948. He was followed by jazz era giants Ella Fitzgerald and Louis Armstrong. Soon the hotels housed their own 20-piece orchestras for all of their stage shows. Everyone got to share in the flow of wealth washing along the talent stream.

Due to the popularity of the headliners, casino owners would offer performers extended engagements, which resulted in the headliners in residence that rock the world to this day. Top talent would be paid an immense amount of money in 1950s dollars, from $50,000 per week in the early 50s, up to $300,000 per week as time passed. Comedian Red Buttons quipped, “Working four weeks in Las Vegas could buy you a Third World country.”

But they were just getting started. Soon a new breed of Vegas entertainers would come to town and burn their names into the registry of Las Vegas legends.

The Rat Pack

After the wave of early jazz and rock and rollers hit Vegas, the Crooners came to town. Popular singers like Frank Sinatra, Dean Martin, and Sammy Davis Jr. each brought his own brand of cool to the Vegas Strip. Slick, stylish, and able to sing crowds into quivering blobs of jelly, the Crooners were the toast of the town. The trio strolled into Vegas not just for a dime, but to have a helluva time.

Known as the Rat Pack, these cool cats usually travelled to Vegas together. If Frank was the headliner at one casino, Dean and Sammy would crash the stage and perform with him, and Frank would return the favor for each of them. And the crowds went wild. The three amigos amazed crowds not only with their croons, but with their hip banter and witty one-liners. Dean once famously held Sammy in his arms and quipped “I’d like to thank the NAACP for this award.”

And what could be better than a stage full of crooner legends in Vegas? A Hollywood film starring crooner legends robbing a Vegas casino. The original Ocean’s 11 (1960) starred the Rat Pack and all of their Vegas pals in a casino heist film.

Viva Las Vegas! The Elvis Years

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Surprisingly enough, the King of Rock and Roll did not crush it when he first appeared on Vegas stages in the mid-50s. Though Elvis topped the charts and shook the music world with his warbling voice and gyrating pelvis, the Strip was not yet ready for him. Vegas of the 50s was ruled by jazz giants and crooners, so the brash young rock and roller scared away the older, more conservative crowds of the day.

Following a legendary televised 1968 Comeback Special, Elvis returned to Vegas to set the nights on fire. He devoted himself to a long-term residency on the Strip, and sold out over 800 shows leading up to his death. His live shows became the stuff of legends, and his famous Vegas years are marked by sequin-encrusted jumpsuits, huge orchestras and choirs, sweaty mutton-chop sideburns, and karate kicks. Soon the name Elvis became inseparable from Vegas, and each left its indelible mark on the other.

Permanent Fixtures

The vast list of legendary Vegas performers cannot fit into one article alone. For special recognition in changing the very face of Vegas entertainment, the award goes to Liberace. Before Elvis saw his first sequin, Liberace wowed the crowds with his personally-designed clothing, capes, and diamonds. This smooth showman swooped over his diamond-decked piano on strings, and would stroll through the audience to show off the giant diamond rings on his fingers. “You like them?” he grinned, “You should, you bought them.” Suave, Mr. L.

Other permanent residents of Vegas include Wayne Newton, who appeared so many times in Las Vegas he was simply referred to as Mr. Las Vegas. He gets popularity points for sheer number of shows played on the Strip: more than 30,000. But the highest grossing acts in the history of the strip weren’t singers. Vaudevillian Vegas embraces sensationalism to the point of absurdity; we’re talking animal entertainment. Where else but Vegas could two men with lions and tigers on stage pull in more than a half billion dollars in over 30 years? Siegfried and Roy did exactly that.

In terms of sheer box office receipts, the most successful entertainer in Vegas history is none other than magician David Copperfield. His box office receipts from Vegas alone total more than $850 million. But in Vegas, fame is measured in more than dollars. Few entertainers have achieved the status of Las Vegas royalty.

Lasting Tribute to Vegas Entertainers

In the ultimate display of respect for Vegas stars who have passed away over the years, the Strip has dimmed its billions of lights in honor of their lives. The Strip has dimmed its lights several times in its bright history, to honor the passing of the entertainers who left a lasting mark on the scene. Among these select few are Elvis Presley, Don Rickles, George Burns, and of course, the Rat Pack: Frank Sinatra, Dean Martin, and Sammy Davis Jr.

If you missed the dimming of the lights in honor of your favorite legendary Vegas entertainer, you can just take a ride down the Las Vegas Strip to cruise down streets named after these icons. The Rat Pack is immortalized in streets named after them. Frank Sinatra Drive, Sammy Davis Jr. Drive, and Dean Martin Drive are a permanent part of the map. Of course the King of Rock and Roll has his own street: Elvis Presley Boulevard.

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After the boom era of Vegas, the entertainment quality slowly slipped down a few notches. After all, Vegas was about gambling over anything else. And the days of mobsters throwing cash at their idols was long gone. Modern moguls ran the casinos like bean counters, and the bottom line was casino cash. Entertainment became just the sideshow. Until online gaming crashed the scene. Now people can gamble from home on their phones and laptops, without the fanfare and travel expenses. And for the first time in history, Vegas numbers started slumping.

A New Generation

The new generation isn’t interested in sitting at slots for hours in a trance like their grandparents. Millennials want more bang for their buck, and that means quality experiences, delivered in responsible and sustainable ways. The casino kings found that the new crop of visitors goes for the shows, the fine dining, and the luxury hotel experience. Gambling became the sideshow. So Las Vegas went back to its roots to bring in the greatest entertainers today. And the crowds started rushing back to the Strip.

The New Vegas Resident Megastars

The new age of megastar entertainers exploded onto the scene in 2003, starting with Celine Dion’s residency ‘A New Day.’ In her four-year Vegas residency, Dion’s shows grossed $385 million at Caesars Palace. Several megastars have managed to cross the generation gap and wow a new group of fans. The undisputed super showman and Knight of the Order of Sequins, Feathers, and Huge Shades, Sir Elton John held court in Vegas for 2 successful residencies, the Red Piano (2004-2009) and the Million Dollar Piano (2001-2018).

And the Knight is not alone. Joining him in the new limelight of Vegas are pop sensations Cher, Jennifer Lopez, Gwen Stefani, and Brittany Spears. Several years ago, in a symbolic torch passing, old Vegas crooner Tony Bennett joined Lady Gaga to record an album of jazz standards from the Great American Songbook. And the Lady went Gaga over the experience. She has since taken her megastar pop status, married it with jazz sensibilities, and taken her show on the road to Vegas.

With the new Vegas artist residencies, Vegas has regained its status as a full-time show town. And while gambling is still the most lucrative business in Sin City, the recent entertainment explosion on the Strip has sent shockwaves around the world, and millions of visitors and Sin Citizens have heard the mighty sound.

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