This weekend, beleaguered British Prime Minister Theresa May was photographed tentatively extending her thumb and pinkie in the “Shaka” sign with a group of less-than-enthusiastic-looking teens at a U.K. music festival. May looked vaguely confused as she flashed the hand gesture, which translates to “hang loose” and is best known as sign language for surfers (as in, “sick cutback, brah”).

The photograph captured May’s attempt to bond with youth volunteers from the state-sponsored National Citizens Service program, one of whom told a local paper he was “just gassing we got the PM to do that.” The irony of a decidedly uncool May signaling a “cool” hand gesture was evidently not lost on him.

But using popular culture to boost political appeal has increasingly become an important strategy for politicians. This weekend’s photo-op shows May embracing that strategy, knowing that appearing cool or hip can transform a politician’s persona.

No one has mastered this more effectively than Barack Obama. As a presidential candidate, he translated his political campaign into a hip brand, selling himself as the (literal) poster boy of “Hope” to enthusiastic and digitally engaged young voters. In 2009, he became the first sitting president to appear on a late night talk show (Jay Leno’s); in 2012, the first sitting president to appear on a daytime talk show (The View), and the first to be interviewed on a podcast (WTF with Marc Maron) in 2015.

Obama appeared on Jon Stewart’s The Daily Show seven times, five of them while he was in office and two times before he became POTUS, including in 2005 when he was still a freshman senator for Illinois. He slow-jammed the news with Jimmy Fallon, delivered the “Decree” on The Colbert Report, and landed jokes in Jerry Seinfeld’s “Comedians in Cars Getting Coffee.” He and former first lady Michelle Obama were on Ellen DeGeneres’ daytime chat show so many times that she made a highlight reel on the last day of his presidency.

The art of translating political messages to popular media has long been referred to as “showbiz politics”—not always in a positive light.

Running against Obama in 2008, Arizona Sen. John McCain released an ad that suggesting that while Obama’s charisma and ability to entertain had made him popular, he was no more fit to run the country than Britney Spears or Paris Hilton.

“He’s the biggest celebrity in the world,” the ad warned. “But is he ready to lead?” Meanwhile, Mitt Romney was making a fool of himself during a Martin Luther King Day parade in Jacksonville, Florida, breaking into a bizarre rendition of the Baha Men’s “Who Let the Dogs Out?” while posing for a photograph with a group of young black people.

Long before Obama came along, Franklin Roosevelt was criticized for mixing “politics and glamor” as a way of wooing voters during his presidential campaign.

Yet the tactic benefited Harry Truman, who succeeded Roosevelt as president two months after he played piano with Lauren Bacall perched atop the instrument for the National Press Club in 1945. Three years later, Bacall and her husband Humphrey Bogart were vocal Truman supporters during his successful campaign for re-election.

John F. Kennedy also used pop culture to woo to voters, both during the primaries (Frank Sinatra reworked “High Hopes” for a JFK ad campaign) and throughout his presidency.

On the other side of the pond, the Harold Wilson cozied up to the Beatles to promote the Labour Party’s political agenda while campaigning to be prime minister in the 1964 general elections. Twenty years later, Labour Party leader Neil Kinnock was criticized by fellow politicians (and hailed by fans) when he appeared in a Tracey Ullman music video.

In the mid-’90s, Geri Halliwell of the Spice Girls controversially declared former Conservative Prime Minister Margaret Thatcher “the pioneer of our ideology—girl power.” When he assumed power Tony Blair held a “Cool Britannia” reception at 10 Downing Street.

Blair later appeared with comedian Catherine Tate in a 2007 sketch for charity telethon Comic Relief, with Tate playing her most famous character, mouthy schoolgirl Lauren, whose refrain “Am I bovvered?” entered the national argot.

Blair’s successor Gordon Brown said he liked the band Arctic Monkeys but couldn’t remember, when asked by GQ, the names of any of their songs. “They’re very loud,” Brown said.

In the U.S., Ronald Reagan’s critics derided his background in Hollywood when he ran for president, but Nancy Reagan’s 1983 appearance on the sitcom Diff’rent Strokes was considered a big moment for her “Just Say No” anti-drug abuse campaign.

Bill Clinton’s 1992 saxophone performance on The Arsenio Hall Show, and later performances on Larry King Live and MTV, were more assured than the Reagans’ faltering embrace of youth culture.

After Obama’s embrace of youth and pop culture worked so well for him, the presidential candidates in the 2016 election desperately attempted to emulate his strategy.

Bernie Sanders surpassed Obama in some respects with his grassroots campaign and calls for “revolution,” landing him the center of a “Berniemania” political youth movement unlike anything America had seen since the 1960s. While many millennials turned their noses up at Hillary Clinton, whose attempts to win youth voters by appearing “cool” and “hip” frequently backfired, they adored Sanders and perceived him authentic.

As with Obama, showbiz strategies—an appearance on Ellen in which he said “Burn, Bernie, Burn” would be an appropriate ice-cream flavor named after him, as well as appearances on Bill Maher and Jimmy Fallon’s shows—worked for Sanders. While one interview between Sanders and his surrogate Killer Mike was criticized by many in the black community, his efforts to maintain his hold on the youth vote were never too try-hard.

The opposite was true for Hillary Clinton (recall her attempts to explain student debt in emoji on Twitter, and her “colored people joke” with New York City Mayor Bill de Blasio). However, her October 2015 appearance on Saturday Night Live as Val the barmaid opposite Kate McKinnon as Clinton herself won plaudits.

Generally, despite the support of the likes of Katy Perry and Lena Dunham, pundits and columnists frequently implored Clinton to stick to what she was good at rather than waste energy trying to appeal to millennial voters and the creative class.

Even with Sanders out of the race and stars like Beyoncé and JAY-Z hosting fundraisers for Clinton, cultural heavyweights and the Democratic-majority millennial vote weren’t enough to defeat Donald Trump in the general election. (Trump’s best-known young advocate, Milo Yiannopoulos, is as divisive as he is.)

As for Theresa May’s “Shaka” photo-op this weekend, even the teens making the gesture in a huddle around her did so half-heartedly. This won’t be a transformative moment for the British PM—not unless she reveals to the U.K. tomorrow that she plays drums and is a big David Bowie fan.