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Vaughn made his television debut on the November 21, 1955 "Black Friday" episode of the American TV series Medic, the first of more than 200 episodic roles by mid-2000. His first movie appearance was as an unaccredited extra in The Ten Commandments (1956), playing a golden calf idolater and also visible in a scene in a chariot behind that of Yul Brynner. Vaughn's first credited movie role came the following year in the Western Hell's Crossroads (1957), in which he played the real-life Bob Ford, the killer of outlaw Jesse James.

Vaughn's first notable appearance was in The Young Philadelphians (1959) for which he was nominated for a Supporting Actor Academy Award. Next he appeared as gunman Lee in The Magnificent Seven (1960), a role he essentially reprised 20 years later in Battle Beyond the Stars (1980), both films being adaptations of filmmaker Akira Kurosawa's 1954 Japanese samurai epic, Seven Samurai. Vaughn played a different role, Judge Oren Travis, on the 1998-2000 syndicated TV series The Magnificent Seven. Vaughn is the only surviving member of the title cast of the original 1960 film (although Eli Wallach, who portrayed the villain Calvera, is still living).

In the 1963-1964 season, Vaughn appeared in The Lieutenant as Captain Raymond Rambridge alongside Gary Lockwood, the Marine second lieutenant at Camp Pendleton. His dissatisfaction with that role led him to request a series of his own. Earlier, Vaughn had guest starred on Lockwood's ABC series Follow the Sun.

Vaughn currently is a spokesman in a set of generic advertisements for various law firms around the U.S. One example is Kalfus & Nachmanin Norfolk, VA. A TV commercial featuring Vaughn urges injured complainants to tell the insurance companies "You mean business." Another law firm in Maine, Joe Bornstein, also uses the Vaughan advertisements with the same slogan.

The Man From U.N.C.L.E.

From 1964 to 1968, he starred as "Napoleon Solo", the man from U.N.C.L.E. ("United Network Command for Law and Enforcement"), with British co-star David McCallum playing his fellow agent Illya Kuryakin. Following the end of that series — which had spawned a spin-off show, large amounts of merchandising, and overseas theatrical movies of reedited episodes — It was in this year that Vaughn landed a large role playing an ambitious Californian politician in the film Bullitt staring Steve McQueen. Vaughn continued to act, in television and in mostly B movies. He starred in two seasons of the Gerry Anderson detective series The Protectors in the early 1970s, and a decade later starred with friend George Peppard in the final season of The A-Team. According to Dirk Benedict, Vaughn was actually added to the cast of that show because of his friendship with Peppard. It was hoped Vaughn would help ease tensions between Mr. T and Peppard.

In 2004, after a string of guest roles on series such as Law & Order, in which he had a recurring role during season eight, Vaughn experienced a resurgence. He began co-starring in the BBC series Hustle, made for the UK's BBC One, also broadcast in the United States on the cable network AMC. In the series Vaughn plays elder-statesman con artist Albert Stroller, a father figure to a group of younger grifters. In September 2006, he guest-starred in Law & Order: Special Victims Unit. Vaughn is a pitchman for personal injury attorneys in television commercials aired throughout the USA.

Vaughn also appeared as himself narrating and being a character in a radio play broadcast by BBC Radio 4 in 2007 about making a film in Prague, Czechoslovakia, during the Russian invasion of 1968. Frequent references are made to his playing Napoleon Solo and the character's great spying abilities.