Bob Montana was born in Stockton, California, but traveled extensively as a child due to his parents' occupations. He spent his school summers in Meredith, New Hampshire, where his father raised vegetables and operated a restaurant and it was there that Bob practiced his cartooning by drawing caricatures of the restaurant's customers. When Bob was 13, his father died of a heart attack, and his mother remarried.

When Bob was 16 years old, the family moved to Haverhill, Massachusetts and for the next two years, he kept diaries of local events and news stories, illustrating the diary pages with his cartoons. The students and faculty of Bob's high school, Haverhill High, would later inspire the leading characters in Bob's most famous creation, the Archie comics.

In his senior year of high school, Bob moved with his parents to Manchester, New Hampshire and graduated from Manchester High School Central in 1940.

Following graduation, Bob moved to New York and attended the Art Students League and the Phoenix Art Institute. He soon began freelancing and created an adventure strip about four teenage boys which he tried to sell without success. Bob started working for MLJ Comics and was eventually asked to work up a high school style comic strip story. At age 21, he created Archie. The success of the character in MLJ's Pep Comics December, 1941 led MLJ to assign Bob to draw the first issue of Archie In November, 1942.

Bob spent four years in the Army Signal Corps during World War II, drawing coded maps, and working on training films. In 1944, while stationed at Fort Monmouth, New Jersey, he met 19-year-old Army secretary, Helen (Peggy) Wherett, a native of Asbury Park, New Jersey. In 1946, the couple married and moved to Manhattan for a short while before returning to Meredith in 1948, where they bought an old New England-style farmhouse. In New Hampshire, they raised four children along with organic vegetables, assorted chickens, horses and sheep.

Bob continued to draw Archie for the rest of his life. After hours at his drawing table, it was his custom to relax by sailing his sloop, the White Eagle, on Lake Winnipesaukee, or skiing cross country near his home. He died of a heart attack on January 4, 1975, while cross-country skiing in Meredith. He was 55 years old.

From 1999 to 2003, his daughter, Lynn Montana, of Meredith, along with her sister, Paige Kuether, managed a website, ArchiePrints.com, to market prints of their father's artwork. The site featured pages from the diary-sketchbook kept by Montana about life in Haverhill High during the late 1930s.

After hours at the drawing table, Montana relaxed by sailing his Friendship sloop, the White Eagle, on Lake Winnipesaukee, and taking cross country ski jaunts through the back country near his home. He died of a heart attack on January 4, 1975, while cross-country skiing in Meredith.