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The Tonight Show’s 30-year host Johnny Carson played many characters throughout his time on the iconic late-night program. And his impersonation of country singer Willie Nelson seemed to be yet another humorous nod to his own real life. What makes Carson’s rendition of “To All the Girls I’ve Loved Before” with singer Julio Iglesias so memorably funny?

Julio Iglesias in a white suite, holding a microphone and looking at Johnny Carson, who is dressed as Willie Nelson
Julio Iglesias and Johnny Carson | Gary Null/NBCU Photo Bank

Johnny Carson’s love life fed the Hollywood rumor mill

Though Carson’s three divorces provided plenty of tabloid fodder and he supposedly disliked the gossip about him, it seems he enjoyed being married more. He spent most of his 79-year life in one union or another and usually wed again relatively quickly after divorce.

In 1949, Carson married his first bride, Jody Wolcott, when he was in his 20s. They had three sons together and those were his only children. But all in all, he married four times before he died.

During three decades as host of The Tonight Show, Carson frequently joked about his love life. And he seemingly saw a good opportunity for a hilarious gag when Iglesias stopped by in 1984 and Carson had been married three times.

Julio Iglesias and Johnny Carson performed ‘To All the Girls I’ve Loved Before’

In a clip available on YouTube, Carson graced the stage dressed as Nelson to sing the duet, “To All the Girls I’ve Loved Before” with Iglesias.

One notable thing about his vocal impression of Nelson is how much he sounds like the country star. Other singers like Dolly Parton and Patsy Cline have said that Nelson has a very unique way of phrasing when he sings. Apparently, it can be hard to recreate, even for professionals.

Despite that — and being able to see a bit of shine from beard tape — Carson arguably nailed the whole impersonation. The audience was in hysterics as he sang lyrics like, “To all the girls who shared my life/ Who now are someone else’s wife/ I’m glad they came along/ I dedicate this song/ To all the girls I’ve loved before.”

As far as what is known of Carson’s personal life in 1984, he was separated from his third wife, Joanna Holland, after they’d married in 1972. According to a report from Associated Press, the couple split in 1982 and divorced in 1985.

They privately agreed to monthly payments of $35,000 for her, which he paid to a total of $2.8 million.

Willie Nelson has also been married four times

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Like Carson, Nelson has attracted attention in his private life throughout many decades as a superstar. Also like Carson, he’s been married four times, with his last marriage being his longest.

In 1986, Nelson met his fourth wife, Annie D’Angelo, and they were married in 1991. They’re still together as of January 2022 and Nelson is now 88.

Notably, Carson married his fourth wife, Alexis Maas, in 1987 and essentially retired from the entertainment industry when he left The Tonight Show in 1992. After that, he seemingly retreated into his hilltop mansion in Malibu where he and Alexis lived until his death in 2005.