Ever since Franklin D. Roosevelt invited Frank Sinatra to the White House for tea, presidents have regularly hobnobbed with pop stars. Sometimes, they click immediately. Members of The Allman Brothers Band, for example, have an extensive friendship with fellow Georgian Jimmy Carter and played his campaign stops. Other times, the collisions of these two high-profile worlds—one defined by youth and coolness, the other by decorum and authority—have been a little uncomfortable. Here are five encounters between presidents and music stars that were somewhat awkward.

1. ELVIS BADGERS NIXON FOR A NARC BADGE.

No one in Elvis Presley’s entourage dared questioned the King in his later, more indulgent years. So, in 1970, when Elvis, listless and sullen in his Los Angeles mansion, announced he wanted to go to Washington, D.C., his personal assistant Jerry Schilling hopped on a red-eye flight with him.

Elvis was a collector of honorary police badges, gifts from law enforcement agencies with whom he was friendly. Schilling soon discovered the reason for the trip was to get a badge from the Bureau of Narcotics and Dangerous Drugs (the precursor to the DEA).

Elvis appealed to the president directly, presenting a handwritten note at the White House gate on the morning of December 21, 1970. He pledged his help fighting anti-establishment sects from the inside. “The drug culture, the hippie elements, the [Students for a Democratic Society], Black Panthers, etc. do not consider me as their enemy,” he wrote to Nixon. “I can and will do more good if I were made a Federal Agent at Large,” he insisted. The note included his hotel and room number. It made its way to aide Egil “Bud” Krogh, a fan, and by noon, Elvis had an appointment in the Oval Office.

According to Krogh’s notes, Elvis restated his support for Nixon and indicated The Beatles as a “force for anti-Americanism.” (They were actually on the same page: Two years later, the Nixon administration tried to deport John Lennon.) Nixon nodded along and stated his concern that Elvis “retain his credibility.”

The meeting ended with a spontaneous hug. Although Nixon never called on Elvis’ services, he did arrange for him to get a narc badge. An aide presented it to him after Presley and his associates ate lunch in the White House cafeteria.

2. GERALD FORD AND GEORGE HARRISON EXCHANGE LAPEL PINS.

In 1974, George Harrison embarked on his first post-Beatles U.S. tour. Attending the November 16 show in Salt Lake City was 22-year-old Jack Ford, whose father assumed the presidency three months earlier following Nixon’s resignation.

On December 13, the Fords welcomed Harrison and his tour mates, including Ravi Shankar and Billy Preston, to the White House. At the time, one of Ford’s major focuses was the WIN (“whip inflation now”) campaign, which encouraged savings and moderate spending habits. Many criticized it for putting the onus on citizens to correct the economy. Alan Greenspan later dubbed WIN “unbelievably stupid.”

Harrison’s saxophonist, Tom Scott, told Rolling Stone in the January 30, 1975 issue (as reprinted in a 2011 issue of Beatlefan) that the president “took us into this little side room where he had all this WIN paraphernalia—posters, watches, sweaters, T-shirts.” It “looked just like the back room at [Harrison’s label] Dark Horse Records, which is loaded with T-shirts and bags and towels.”

Ford took the opportunity to stick a WIN button on Harrison’s lapel. Harrison gave Ford a button of his own, reading “om,” a sacred sound in Indian religions. Harrison also jammed on the White House piano and posed for a picture in Ford’s seat in the Cabinet Room.

3. REAGAN GIVES MICHAEL JACKSON A PUN-TASTIC INTRODUCTION.

The face of music in the ’80s was Michael Jackson. The defining figure of politics that decade was Ronald Reagan. For one afternoon, the two were side-by-side.

On May 14, 1984, Reagan invited Jackson to the White House to present him with the Presidential Public Safety Communication Award for allowing “Beat It” to be used in a public service announcement against drinking and driving.

Always the joker, the 73-year-old president’s introduction included repeated references to Jackson’s work, no doubt the work of a young speechwriter:

“I hope you'll forgive me, but we have quite a few young folks in the White House who all wanted me to give you the same message. They said to tell Michael, ‘Please give some TLC to the PYTs.’ Now I know that sounds a little ‘off the wall,’ but you know what I mean. And, Michael, I have another message from our fans in the Washington, D.C., area. They said, ‘We want you back.’ So when you begin your greatly awaited cross-country tour, will you please be sure to drop off here in the nation's capital?”

Of meeting Jackson, Reagan wrote in his diary that he “was surprised at how shy he is.”

4. GEORGE W. BUSH MISTAKES U2's BONO FOR CHER'S EX-HUSBAND.

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When George W. Bush came into office, Bono, the lead singer of U2, had been advocating the elimination of third-world debt. According to the Guardian, he racked up meetings with officials from the newly installed Bush administration, including Colin Powell and Condoleezza Rice. He also recruited to the cause evangelical leaders, like Rev. Billy Graham, who were allied with Bush. In fact, it was 80-year-old conservative Senator Jesse Helms who convinced Bush himself to meet with Bono.

Before the singer’s March 2002 appointment in the Oval office, an aide told the president, “Bono’s coming. You do know who he is?’” Bush recalled in a 2015 documentary.

Bush retorted, “Sure, he’s married to Cher.”

Of course, Bono of U2 was not Sonny Bono, the American singer/songwriter who was half of Sonny and Cher, a couple who had been divorced since 1975. Also, though he was politically active, having been elected three times to Congress, Sonny Bono had been dead for four years at the time of the meeting.

Nonetheless, the U2 frontman won him over. Soon, Bush was pushing for a $5 billion aid package, with the singer’s active support. Bono met with Bush on several other occasions and accepted his invitation to speak at the 2006 National Prayer Breakfast.

Hopefully, at some point, someone lent Bush a copy of Achtung Baby.

5. BOB DYLAN IS TOO COOL TO HANG OUT WITH OBAMA.

On February 9, 2010, the White House staged a concert to celebrate the civil rights movement. On the bill were Joan Baez, Jennifer Hudson, John Mellencamp, Smokey Robinson, Natalie Cole, Yolanda Adams, and Bob Dylan.

Dylan didn’t show up for rehearsal or the meet-and-greet before the show.

“He didn't want to take a picture with me,” Obama told Rolling Stone in 2010. “Usually all the talent is dying to take a picture with me and Michelle before the show, but he didn't show up to that.”

Organizers had asked Dylan to play a song, but they were not sure which he would play. When showtime came, Dylan, with a bassist and pianist, went on and performed “The Times They Are A-Changin’." Obama’s first encounter with the musical icon came after the song was finished.

“[He] steps off the stage—I'm sitting right in the front row—comes up, shakes my hand, sort of tips his head, gives me just a little grin, and then leaves," Obama told Rolling Stone. "And that was it—then he left. That was our only interaction with him.”

The president, a fan, was OK with it. “That's how you want Bob Dylan, right? You don't want him to be all cheesin’ and grinnin’ with you.”

Two years later, Dylan returned to the White House and tolerated Obama pinning the Medal of Freedom on him.