Anyone who believes that watchmaking should be serious business — and reflect centuries of history and tradition — should stop reading now.

In recent months the watch industry has been introducing fun, irreverent timepieces, and the kookier, the better.

Headlining the trend is Richard Mille’s RM 88 Automatic Tourbillon Smiley, a tribute to 50 years of the Smiley face image, which Franklin Loufrani, then a French journalist, designed and registered in 1971.

Priced at 1.1 million Swiss francs (the equivalent of about $1.16 million) and limited to 50 pieces, the skeletonized RM 88 features a prominent yellow-gold Smiley face that’s painted on the dial and then microblasted, along with a host of other feel-good motifs: a rainbow in varnishes applied by hand; a gold cocktail glass that was partly microblasted to give it a chilled look, complete with a gold umbrella, olive and a grooved straw just 0.4 millimeters wide; a pink flamingo with an eye created by one of the world’s smallest beading tools; a pineapple; a cactus; and a sun.

Three years in the making and powered by a specially designed CRMT7 movement that was made in-house, the watch was an “unexpected fun project, as bold as it is highly technical,” Alexandre Mille, Richard Mille’s chief executive, wrote in an email.

The brand hopes that the design will be a constant boost to its owners. “Everything that can bring a (literal!) smile to your face or a moment of joy, can be like a bit of sunshine,” Mr. Mille wrote.

“A watch that makes me smile” is how enthusiasts often describe their love of certain pieces.

That sentiment was likely to be behind the recent spate of watches with cartoon characters, which included Snoopy cavorting on dials by Omega, Timex and Bamford London (which also had Big Bird and Popeye), while Audemars Piguet, in collaboration with Marvel, added a sculpted Black Panther to its Royal Oak in a limited edition last year.

Sometimes the character doesn’t even appear in person. The reference numbers of some of the most desirable Rolexes, for example, are mysteries as the timepieces are much better known by their cartoon character nicknames, inspired by the colors of the dials or the bezels or both: Batman, a GMT-Master II with a blue and black bezel; the Hulk, a Submariner with (of course) a green dial and matching bezel; Smurf, a white-gold Submariner with a blue dial and matching bezel; and Pikachu, an Oyster Perpetual with a yellow dial.

“If the collecting community gives something a nickname,” said Paul Boutros, head of watches for Americas at Phillips, “it can really change the fortunes of a model or watchmaker.”

Mr. Boutros also credited fun watches, such as the “happy and just outlandish” RM 88, with expanding the market in general. “Watches are irrelevant — they are an anachronistic object,” he said. “But we want them to thrive and succeed for the foreseeable future, so doing different things that are out of the box helps keep them in people’s mind and in the conversation.”

Gary Getz, a retired management consultant who writes a watch collecting column for Quill & Pad, knows about fun in horology. While he collects such serious, mainstream brands as Patek Philippe, Greubel Forsey and MB&F, he also favors offbeat brands, like that of the Russian watchmaker Konstantin Chaykin.

Mr. Getz owns the first Joker, a watch that Mr. Chaykin named for the DC Comics’ character. It tells time via two rotating disc “eyes” — one for hours, the other for minutes — that appear to focus in different directions for much of the day, creating a googly-eye expression. The red tongue, in the smiling mouth, is a moon phase indicator.

The Joker and the Wristmons line that followed — what the brand calls its “mechanical monsters on the wrist” — now include many humorous iterations, from a Minotaur to a bright yellow Minions character.

Mr. Chaykin’s pieces are nominated regularly for the Grand Prix D’Horlogerie de Genève, the annual industry awards event. This year, for example, the 2022 model depicting the Joker’s girlfriend, Harley Quinn, was nominated in the ladies’ category (19,950 Swiss francs; limited to 28 pieces).

Mr. Getz said he bought the Joker when it debuted at the 2017 Baselworld watch fair, a year when high-end watch sales were declining and, he recalled, “the China market was in the tank.”

“The Joker was exactly the right watch for the moment,” he said. “Everyone smiled when they saw the watch, and thought that maybe things will be all right. That watch was a real tonic in a kind of glum time.”

But perhaps the most amusing watch in Mr. Getz’s collection is a much cheaper piece with a dial that shows a Max Headroom-like rendering of Mr. Getz’s face: a C.G.I.-style portrait overlaid on a background of black and white rays.

Mr. Getz had posted the original cartoon on Facebook, prompting a colleague to comment that his worst nightmare would be to see that image on a watch. Mr. Getz accepted the challenge and found a company on Google that charged $55 to put it on the dials of two timepieces. Mr. Getz gave one to his colleague and kept the other, which today he calls “The Greatest Watch Ever Made.” He regularly wears it to watch fairs and meetings with watch chief executives and other managers.

“They all think it’s hilarious,” Mr. Getz said. “But they know that only I would wear this cheap, knockoff watch with my own face on it as a cartoon — and pretend to be proud of it.”

Fun watches, after all, are rooted in self-expression. The Washington, D.C.-based watch collector Abduljabar Totonji bought his Joker sight unseen after first coming across it on social media, and the piece became his collection’s third watch (preceded by a Rolex GMT-Master II and Omega Speedmaster).

“The Joker spoke to me and I just felt like I had to have one in my collection,” said Mr. Totonji, who added that he sees himself as a fun person who enjoys meeting people (he regularly hosts watch collector meet-ups in the Washington area). “I try not to take myself too seriously and try to enjoy myself with the collecting as well.”

Mr. Totonji likes unusual watches that tell time in an esoteric way — like his Raketa Russian Code, that runs counterclockwise — but he also has been drawn to independent watchmakers because they resonate with him professionally (he is the chief investment officer at a real estate investment business that has just 15 employees). “I take my work seriously — and I know they take their work seriously,” Mr. Totonji said.

Humor is infectious, and so, too, is sharing the joke of an irreverent watch with others.

Marko Koncina, the Zurich-based founder of the watch media platform Swiss Watch Gang, owns a Joker as well as the new Sequent Smart(ass). The smartwatch (priced at 545 pounds in Britain, $549 in the U.S. and limited to 160 pieces) was codesigned with the French artist and watch collaborator Romaric André, known as seconde/seconde/, and was intended as a cheeky motivational piece, featuring a step counter whose indicators say, “Shut Up, Push Harder,” and other off-color exhortations.

When it comes to the Joker, people “either think it’s super expensive or a child’s toy,” Mr. Koncina said. “For me, I don’t care. But when there’s that one person who knows what it is, we connect immediately. We’re like brothers.”

The fun trend isn’t limited to haute horlogerie, either. The niche, London-based maker Mr Jones Watches has created playful designs mostly priced at less than $300 ($645 is the most expensive model) that aim to make timekeeping lighthearted. “It’s about bringing a kind of moment of joy back into what can be quite a prosaic thing,” said Crispin Jones, the brand’s founder. “We like to say our watches are more like time on a human scale.”

Its latest watch, Beam Me Up!, for example, was codesigned with the children’s book author-illustrator Xavier Broche. It imagines an alien spaceship searching for life on a farm, where a pig and the flying saucer’s beam indicate the hours and minutes, respectively. A brown nubuck strap adds an “Americana theme of Roswell, Area 51 alien abductions” feel to the watch, Mr. Jones said.

Signs are increasing that fun watches are becoming mainstream, if the fashion brands are any indication.

At Gucci, the house has celebrated 50 years of its Swiss-made watches with a special film that imagines the house’s high watchmaking models as rides and games at a magical fairground.

Louis Vuitton’s Tambour Slim model (priced at $96,000) also embraces gaming, with the house mascot, Vivienne, at the center of a jumping hours watch in three personas: a fortune teller, a casino croupier and a circus juggler, complete with matching bejeweled motifs like tarot and playing cards.

Hermès has been bringing a tongue-in-cheek approach to its watches for more than a decade, thanks to dial images taken from some of the house’s celebrated silk scarves. There has been the Arceau Pocket Aaaaargh!, a minute repeater and tourbillon pocket watch with a dial that depicts a Tyrannosaurus’s face in a leather marquetry mosaic, while the Slim d’Hermès Grrrrr! zooms into a miniature enamel of a bear’s face.

The new Arceau Hermès Story takes after a scarf designed by the English designer John Burton. Its dial, painted on mother-of-pearl, shows an 18th-century equestrienne in wig, mask and ball gown astride a wooden horse and gripping a selfie stick to snap her companions, which include a toucan, turtle and a rabbit.

Philippe Delhotal, artistic director of Hermès Horloger, called Hermès’ watch dials a “playground” for artists, and said that the new watch presented notions of freedom, daring and fun.

“The idea was to bring fantasy and a light tone of voice to the collection,” he said in a video call. “In watchmaking and in Hermès globally, we do things seriously, but we don’t like to take ourselves too seriously.”