In a move that was perhaps inevitable, America’s biggest male reality star met with… the husband of the biggest female one.

That’s right, according to multiple sources, “old friends” Donald Trump and Kanye West convened at Trump Tower this morning to discuss “life” and Kanye becoming an “ambassador of sorts” in some “entrepreneurial leadership role.” One result was the priceless photo above. Another was the handshake below, which, it must be said, was much better executed than Kanye’s embrace with, say, John Mayer.

Time will tell what this meeting will lead to—Mr. West heading up the Department of Emoji Autocorrect, perhaps?—but sometimes celeb-prez pairings actually click. Witness these seven instances when the commander-in-chief and a famed constituent genuinely connected—for a time, anyway…

1
Franklin Pierce and Nathaniel Hawthorne
Nathaniel Hawthorne’s The Scarlett Letter remains widely read today. His 1852 book The Life of Franklin Pierce is a bit less so. The two had been friends since their school days and would literally be close for the rest of Hawthorne’s life, as Hawthorne emerged as a brilliant author and Pierce unexpectedly became President. We at Made Man are fascinated by Pierce, who boasted great hair and lived the grimmest life of all our presidents. His miseries included his own party refusing to let him seek reelection, watching all three of his children die before age 12 and alcoholism. (If you want to feel better about yourself, study Franklin Pierce.) Ironically, Hawthorne dealt his dear friend another tragic blow as, in a twist far too horrible for fiction, Pierce was the one who discovered his dead body.

2
Teddy Roosevelt and John L. Sullivan
Roosevelt was a highly educated member of an extremely rich family who loved books and was prone to doing things like moving to North Dakota to be a cowboy. Sullivan was born to parents who’d fled the Potato Famine and had a knack for “womanizing, brawling and run-ins with the law.” But they had something in common: boxing. The “Boston Strong Boy” was by far the most celebrated fighter of his day and Roosevelt a massive fan. (He even sparred with staff in the White House until a punch nearly blinded him.) A mutual admiration ensued and Sullivan became one of the first Irish-Americans to be a semi-regular at the White House. Remember, Roosevelt left office in 1909 and JFK didn’t arrive until 1961. Speaking of which…

John F. Kennedy and Frank Sinatra
John F. Kennedy and Frank Sinatra
Our coolest president and the Chairman of the Board were bound to hit it off. Theirs was a friendship based on good times and chasing broads, but it was torn apart by concerns Sinatra’s mob connections could damage Kennedy’s political fortunes. (Though there are also allegations that Sinatra’s mob connections actually helped Kennedy’s political fortunes.) Kennedy’s still shocking assassination ended any hope of reconciliation. Distraught over JFK’s death, Sinatra allegedly pulled his classic thriller The Manchurian Candidate (with its tale of a presidential candidate and an assassin) from circulation as a gesture of respect.

feature39Richard Nixon and Elvis Presley
With a solid 77 percent on Rotten Tomatoes, Elvis & Nixon (starring Michael Shannon and Kevin Spacey) celebrates the legendary meeting of Richard Nixon and Elvis Presley in 1970, which produced the strangest Oval Office photos we shall ever see (until it’s revealed Bill Clinton filmed his escapades with Monica Lewinsky). By all accounts, it was a surreal encounter, perhaps best summed up by Nixon’s comment on Presley’s wardrobe: “You dress kind of wild, don’t you, son?” To which Elvis replied, “Mr. President, you’ve got your show to run and I’ve got mine.”

Ronald Reagan and Rock Hudson
Ronald Reagan and Rock Hudson
Reagan, his wife Nancy and Hudson were all actors in Hollywood from the 1940s through the ’60s. Apparently deciding you can only do so many movies opposite a monkey, Reagan turned to politics and claimed the presidency in 1980, while Hudson continued a career that brought him four Golden Globes and an Oscar nomination for Giant (with Elizabeth Taylor and James Dean). In 1984, Hudson attended a state dinner at the White House, where the major Reagan supporter sat at the First Lady’s table. By this point he was dying of AIDS. Gay but closeted, Hudson kept his condition a secret. In 1985, he finally reached out to see if the President could help him gain admission to a top French hospital. Nancy personally addressed the request, accepting a staffer’s recommendation not to act and avoid the appearance of bias, though Ronald did phone Hudson. (In general, the Reagan administration has been criticized for their slow response to the AIDS crisis.) Hudson died nine weeks later at 59.

gbGeorge W. Bush and Rafael Palmeiro
Bush served as the managing general partner for an investor group that acquired the Texas Rangers in 1989 and kept the position until he was elected governor of Texas in 1994. During most of this time the team’s first baseman was Rafael Palmeiro, who seemed a lock for the Hall of Fame with over 500 home runs and 3,000 hits. Then came a positive steroid test and subsequent suspension in 2005. (Particularly awkward because he’d recently said this in front of Congress.) Bush was one of his most vocal supporters, declaring in 2005: “Rafael Palmeiro is a friend. He testified in public, and I believe him. He’s the kind of person that’s going to stand up in front of the klieg lights and say he didn’t use steroids, and I believe him. Still do.” The slugger isn’t the only alleged juicer to call Bush a pal: Before Dubya left office, some speculated he might pardon Roger Clemens.

Bill Clinton and George H.W. Bush
Bill Clinton and George H.W. Bush
Hey, who’s a bigger celeb than a fellow prez? When Clinton defeated Bush Sr. in 1992, it didn’t seem like they were going to wind up best buds: during the campaign’s homestretch, Clinton said Bush was a man who has “no core of convictions” and “would do or say anything to get elected,” while Bush dismissed Clinton and his running mate Al Gore as “two bozos.” Yet they bonded during relief efforts after the 2004 Indian Ocean tsunami. Bush Sr. admitted wondering why Clinton “can’t stay on time” as their schedule was shredded, but concluded: “You cannot get mad at the guy.” Clinton and Bush Jr. have also struck up a friendship and Clinton has joked about getting the Bushes to “adopt Hillary.” Dubya summed up the strange closeness of the families with a quip after Clinton’s heart surgery: “When he woke up, he was surrounded by his loved ones: Hillary, Chelsea and my dad.”