In 1961, 18-year-old Ross enlisted in the United States Air Force and was put into service as a medical records technician. He rose to the rank of master sergeant and served as the first sergeant of the clinic at Eielson Air Force Base in Alaska, where he first saw the snow and mountains that later appear as recurring themes in his paintings. He developed his quick painting technique during brief daily work breaks. Having held military positions that required him to act tough and mean, “the guy who makes you scrub the latrine, the guy who makes you make your bed, the guy who screams at you for being late to work”, Ross decided he wouldn’t raise his voice when he left the military.

Ross and Ridge’s marriage ended in divorce in 1977. Ross and his second wife, Jane, had no children together. In 1992, Jane died of cancer. In 1995, two months before his death, Ross married for a third time, to Lynda Brown.

Ross was working as a part-time bartender when he discovered a TV show called The Magic of Oil Painting, hosted by German painter Bill Alexander. Alexander used a 16th-century painting style called “alla prima” (Italian for “first attempt”), widely known as “wet-on-wet”, that allowed him to create a painting within thirty minutes. Ross studied and mastered the technique, began painting and then successfully selling Alaskan landscapes that he would paint on novelty gold-mining pans. Eventually, Ross’s income from sales surpassed his military salary. He retired from the Air Force in 1981 as a master sergeant.

Ross was fond of country music and in 1987 was invited on stage by Hank Snow at the Grand Ole Opry in Nashville, Tennessee. The audience gave him a huge ovation; he was slightly nervous at first, but felt better after cracking a joke to the crowd. Snow was later given a private painting lesson by Ross.

Ross visited New York City to promote his hardcover book, The Best of the Joy of Painting with Bob Ross, and painting techniques to a studio audience several times. On one visit in 1989, he appeared on The Joan Rivers Show. He returned in 1992 for a live show with hosts Regis Philbin and Kathie Lee Gifford. In 1994, Ross appeared on the Phil Donahue Show and took five audience members on-stage to do a painting. Donahue also did a painting during that episode.

Ross dedicated the first episode of the second season of The Joy of Painting to Bill Alexander, explaining that “years ago, Bill taught me this fantastic [wet-on-wet] technique, and I feel as though he gave me a precious gift, and I’d like to share that gift with you.” As Ross’s popularity grew, his relationship with Alexander became increasingly strained. “He betrayed me,” Alexander told The New York Times in 1991. “I invented ‘wet on wet’, I trained him, and … he thinks he can do it better.” Art historians have pointed out that the “wet-on-wet” (or alla prima) technique actually originated in Flanders during the 15th century and was used by Frans Hals, Diego Velázquez, Caravaggio, Paul Cézanne, John Singer Sargent and Claude Monet, among many others.

In 1995, a visibly ill Ross made his final public television appearance as a guest on the pilot episode of the children’s series The Adventures of Elmer and Friends. The series premiered in 1996, one year after Ross’s death. The episode included a final message of thanks from Ross to his fans and viewers and a musical tribute.

Ross died at the age of 52 on July 4, 1995 due to complications from lymphoma. His remains are interred at Woodlawn Memorial Park in Gotha, Florida under a plaque marked “Bob Ross; Television Artist”. Ross kept his diagnosis a secret from the general public; his lymphoma was not known outside of his circle of family and friends until after his death.

Ross was very secretive about his life and had a great liking for privacy. Some of only a few interviews with his close-knit circle of friends and family can be found in the 2011 PBS documentary Bob Ross: The Happy Painter. Bob Ross Inc. is protective of his intellectual property and his privacy to this day.

Google celebrated the 70th anniversary of his birth with a Google Doodle on October 29, 2012. It portrayed Ross painting a depiction of the letter “g” with a landscape in the background. A board game titled Bob Ross: The Art of Chill was released and carried by Target stores, while a Chia Pet model in Bob Ross’s likeness was also released. Ross was going to have a video game released on Wii, the Nintendo DS and PC, with development handled by AGFRAG Entertainment Group, although this never came to fruition.

In 2014, the blog FiveThirtyEight analysed 381 episodes in which Ross painted live, concluding that 91% of Ross’s paintings contained at least one tree, 44% included clouds, 39% included mountains and 34% included mountain lakes. By his own estimation, Ross completed more than thirty thousand paintings. His work rarely contained human subjects or signs of human life. On rare occasions, he would incorporate a cabin, sometimes with a chimney but without smoke, and possibly unoccupied.

Newfound interest in Ross occurred in 2015 as part of the launch of Twitch Creative. Twitch hosted a nine-day marathon of The Joy of Painting beginning on October 29 to commemorate what would have been Ross’s 73rd birthday. Twitch reported that 5.6 million viewers watched the marathon and, due to its popularity, created a weekly rebroadcast of one season of The Joy of Painting each Monday. A portion of the advertising revenue was promised to charities, including St. Jude Children’s Research Hospital.

In June 2016, Ross’s series Beauty Is Everywhere was added to the Netflix lineup. The 30-minute episodes are taken from seasons 20, 21 and 22 of the original The Joy of Painting series. The newfound interest surprised the Kowalskis, since they were managing Ross’s image and The Joy of Painting episodes. They created a YouTube channel for Ross which gained more than a million subscribers within a year.