We often equate artists with one distinct style. But John Holladay, originally from the Midwest and for many years now a resident of Vineyard Haven, paints and illustrates with so much versatility, he’s impossible to pigeon- hole.

And yet one of his hugely successful, largely unknown artistic endeavors is now being celebrated at the Louisa Gould Gallery on Main street, Vineyard Haven. From 1980 to 2000 he was licensed to paint the official artwork for NBA, NFL and college sports teams, work that later appeared on posters, shirts and jigsaw puzzles.

A John Holladay sports portrait, such as the Babel-tower-sized stadium for Michigan football, replete with hundreds of fans, normally took the artist a week to illustrate and another couple of weeks to colorize.

In a recent interview at the gallery the artist, wearing glasses and a wide smile, described how illustrators must woo sports executives to land the coveted contract: “There’s wining and dining involved.”

Once the artist receives the greenlight, he talks to players and fans and studies yearbooks. Various rules must be adhered to; for instance, at Texas A & M, no caps are allowed in the stadium, and therefore none may be pictured in the poster of hundreds of fans. Another team, whose name shall remain anonymous, required Mr. Holladay to leave out breasts on female fans. (Only a thorough search of the illustrator’s many posters could turn up these anatomically incorrect ladies.)

Mr. Holladay’s paintings are continuously on display at Louisa Gould, but this weekend will yield a reception in honor of the sports work. “I had all the original paintings these past years stashed in a drawer,” Mr. Holladay said. “It suddenly occurred to me that when I’m no longer here, these works will be essentially orphaned.” (He has no children, by the way, but he does own a cherished black and white boxer named Ansel Adams).

So now the sports paintings have been removed from the drawer, framed and put on display for sale. One team dear to New Englanders’ hearts was conspicuously missing from Mr. Holladay’s considerable output: the Boston Red Sox. To rectify this situation, he recently painted the beloved exterior of Fenway Park, with pennants, fans and trees and a noticeable lovability that Red Sox Nation brings to this monument. At this moment, posters for the Fenway masterwork are not available. However, a fair amount of begging on the part of this Gazette correspondent may have given the artist and Ms. Gould an impetus to reproduce the image. Meanwhile the painting itself is priced at $10,000.

From the earliest age, Mr. Holladay loved to draw. His dad was in the Air Force, so the family moved all over the country, with young Holladay later enrolling in college in Iowa. He majored in art education. He has always taught art in addition to creating it, even now commuting each weekday to Falmouth High School. Next Monday he travels to Washington, D.C., to pick up his second annual Scholastic Art Award for teaching.

“Because of my crazy commute during the week, I paint on weekends from morning till night. I never go on vacation because, for me, painting is the highest form of recreation.”

His parents had always discouraged his dreams of becoming an artist. Even when he started selling his earliest landscapes, Mom and Dad refrained from hanging their son’s paintings on their walls. “Until their friends started to buy my art,” he confided with a chuckle. “After that they were very supportive of me.”

Now at the Louisa Gould Gallery, in addition to the sports originals, Mr. Holladay has landscapes in oils, watercolors, acrylics, cartoon illustrations (some small items priced as low as $20), and monochromatic schemes. He can paint with exquisite representational precision or wield a brush and knife to a Vineyard vista and anoint it with just a touch of abstraction. He also favors realism over quaintness: “Most artists portray Menemsha with all the junk missing. I love to keep the junk in,” such as unruly stacks of lobster traps.

The artist brings a joie de vivre to his profession, as well as that tiny bit of outlaw mentality that lurks in so many people of an artistic temperament. When visiting the Island back in 1988, he noticed dinghies were painted an assortment of colors. When he returned to the Midwest, he began to paint barns purple, gold, green, and all the other colors of the rainbow. He found an appreciative customer base for the liberties he’d taken.

And then there’s his own Where’s Waldo element in the sports stadiums.

Mr. Holladay doesn’t stop with a single wild card character in his audience of hundreds. He pops in whoever comes to mind — Batman, Mother Theresa, the Wizard of Oz, Prince Charles, the Statue of Liberty, Oprah, Dick Tracy, Frankenstein. Rather than searching for Waldo, a viewer could spend an hour picking out every famous personality, real or fictitious.

Blessed are those who have so much fun with their work, plus the talent to keep it going. The show continues through June 21.

The artist’s reception for John Holladay’s sports show will be held on Saturday, May 28, from 5 to 7 p.m. at the Louisa Gould Gallery on Main street in Vineyard Haven.