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The art world was stunned earlier this month when a Japanese billionaire paid Sotheby’s $110.5 million for a Jean-Michel Basquiat painting of a black skull. The purchase reset the record for a U.S. artist at auction and infused the beleaguered art market with a shot of adrenaline. Now, the Basquiat’s newcomer buyer—41-year-old e-commerce mogul Yusaku Maezawa—is getting a closer look by the art establishment.

After the sale, art adviser Elizabeth Jacoby of BSJ Fine Art said she started following Mr. Maezawa on social media (his Twitter handle is @yousuck2020), liking images of his private jet because she thinks the racing stripes he recently added match the blue hue of his Basquiat. Major collector Peter Brant recently hosted Mr. Maezawa at his home and art showroom in New York and Greenwich, Conn., where Mr. Brant said the pair looked at Mr. Brant’s Basquiats and chatted through an interpreter. “I could tell by the look in his eyes that he got it,” Mr. Brant said of the artist’s appeal.

Expect galleries and art fairs the world over to look out for any sign of him as well. In the past, art-buying newcomers like Russia’s Roman Abramovich and China’s Yang Bin used art-fair purchases to help propel themselves into the global ranks of heavyweight collectors.

Mr. Maezawa appears to be taking the attention in stride. “There’s nothing wrong with using the money that you earn to be daring and buy art that you love or that you think is beautiful,” he said Friday, sitting in his elegant, two-story apartment in Tokyo surrounded by 1950s French furniture and works by other artists like George Condo, Roy Lichtenstein and Willem de Kooning.

Mr. Maezawa’s movements matter because dealers say his art purchases over the past year have almost single-handedly shifted prices skyward for Basquiat. The Brooklyn artist’s graffiti-style paintings of kings, boxers and skulls in 1980s New York rarely sold for more than $5 million apiece a decade ago. Buoyed by baby boomers and curators who admired the political potency of his art, Basquiat’s auction high bar four years ago stood at $48.8 million for a painting of drug users called “Dustheads.” Dealers at the time considered it a frothy, hard-to-match price.

A year ago, Mr. Maezawa entered the auction arena, paying Christie’s a record-setting $57.3 million last May for a larger, untitled Basquiat that featured a devil. In November, he paid Christie’s $22.6 million for a rainbow-color Pablo Picasso portrait, “Head of a Woman (Dora Maar).” Privately, he started buying works by sculptor Alberto Giacometti and On Kawara, a Japanese artist known for painting dates like time stamps on monochrome backgrounds. Earlier this month, the collector topped himself—and broke Basquiat’s record again—with Sotheby’s $110.5 million skull.

Ms. Jacoby and her art-adviser mother Beverly Schreiber Jacoby said Mr. Maezawa’s recent spree could convince Basquiat collectors that their own examples are worth millions more overnight, tempting others to join a sell-now bandwagon that could backfire if additional buyers fail to join Mr. Maezawa in future competition.

On the other hand, Mr. Maezawa’s emergence could portend a resurgence of Japan’s interest in contemporary art, she said. It has been a quarter-century since the bursting of the Japanese economic bubble mostly put a halt to showy art purchases by the nation’s industrialists. The most notorious was the $82 million purchase in 1990 of Vincent van Gogh’s melancholy “Portrait of Dr. Gachet” by a Japanese paper magnate who suggested he might have the painting cremated and buried with him. He was later arrested in an unrelated scandal and the painting was sold. “Maezawa is a powerful indication of something more significant than the Basquiat market if it means Japan is back to collecting on a global level,” Ms. Schrieber Jacoby added.

A boyish-looking former rock drummer, he amassed a $3 billion fortune selling imported records—and later, trendy clothes—through his online fashion conglomerate now folded under a parent company, Zozotown. Mr. Maezawa said he was introduced to art through music and his first art purchase, at age 25, was a portrait of Kurt Cobain and Radiohead’s Thom Yorke for about 2 million yen.

He still gravitates to portraits over landscapes or abstraction. “For painting, I like strong lines,” he said, “powerful pieces.”

Today, he’s built up a collection of several hundred pieces of modern and contemporary art, plus a group of antique Japanese teacups, examples of which he posts to his Instagram alongside paintings he has bought like Richard Prince’s $9.7 million “Runaway Nurse.” Unlike some seasoned collectors who enlist advisers and curators to oversee their art buys, he said he prefers to shop alone, often online. “I ask a gallery as soon as I find something nice on the Internet,” he said. Auction houses send him catalogs, and that is how he spotted the Basquiat.

When it comes to describing the fight for his latest prize, he seems equally nonchalant. As Sotheby’s evening sale kicked off in New York on May 18, Mr. Maezawa said he was at home in Tokyo. Instead of eating breakfast, he said he watched a live stream of the auction and lobbed his bids by phone to a Sotheby’s specialist who was in the saleroom. This time, he wasn’t shopping alone. He said around 10 members of his staff were standing in his living room—“They looked more nervous than me,” he said—until the gavel fell and he won. “I felt excited.”

Corrections & Amplifications
Yusaku Maezawa was seated next to ‘Cross-Legged Figure’ by Willem de Kooning. A photo caption incorrectly spelled the name of the artist as Wellem de Kooning in an earlier version of this article. (May 26, 2017)