Clint Eastwood and Don Rickles
Clint Eastwood and Don Rickles, two iconic figures in American entertainment, had their paths cross in interesting ways, despite their vastly different personas.
​
Despite their different styles the two men shared a strong friendship. Rickles often made Eastwood a target of his on-stage jokes, especially in his famous celebrity roasts. Eastwood, known for his tough, silent demeanor, became a perfect subject for Rickles’ humor, and the dynamic between the two was both humorous and unexpected.
​
Rickles would often joke about Eastwood’s tough-guy persona, riffing on how Eastwood never seemed to smile or show emotion. Eastwood, with his trademark cool, would always take Rickles’ jabs in stride, showing his ability to laugh at himself. Their friendship was a testament to how Rickles’ humor could cut through the toughest exteriors.
​
One famous moment that illustrates their bond happened at the AFI Life Achievement Award ceremony in 2009, where Rickles roasted Eastwood. Rickles teased Eastwood, saying: "Clint, you’re a legend. This man made some of the greatest Westerns of all time. Clint, you’ve done a lot for the country. You’ve given us some great moments, some great films, and… now you’re old."
​
One notable connection between Clint Eastwood and Las Vegas was the filming of his 1989 movie "Pink Cadillac," in which several scenes were shot in the city. Eastwood’s presence in Vegas, even when tied to movie productions, brought star power to the entertainment capital. Vegas has always been a place where Hollywood figures found themselves—whether for filming, gambling, or just enjoying the nightlife
​
Don Rickles, often dubbed "Mr. Warmth" (ironically, due to his insult comic persona), was one of the most famous comedians in Las Vegas history. Known for his razor-sharp wit and ability to "roast" celebrities and audience members alike, Rickles built a legendary career performing in Las Vegas from the 1950s onward. His biting humor, quick comebacks, and willingness to insult anyone—no matter how famous or powerful—made him a staple in Vegas showrooms for decades.
​
Rickles performed at nearly every major venue in Las Vegas, including the Sahara, the Desert Inn, and later, Caesars Palace. His shows became a must-see attraction in the city, where celebrities and tourists alike would flock to watch Rickles work his magic on stage. No one was safe from Rickles’ humor, and that included some of his close friends, like Clint Eastwood.​
