He also appeared in films such as Magnum Force (1973), Julia (1977), Capricorn One (1977), The Fog (1980), Creepshow (1982), Wall Street (1987), The Firm (1993), Hercules (1997) and Men of Honor (2000).

[1] In 2009, he received critical acclaim for his performance as recently retired farmer Abner Meecham in the independent film That Evening Sun.

[12] From 1942 through 1946, Holbrook served in the United States Army in World War II, achieving the rank of staff sergeant; he was stationed in Newfoundland,[13] where he performed in theater productions such as the play Lady Precious Stream.

[19] In 1968, he was one of the replacements for Richard Kiley in the original Broadway production of Man of La Mancha, although he had limited singing ability.

[19] In 1966, Holbrook starred opposite Shirley Booth in the acclaimed CBS Playhouse production of The Glass Menagerie.

[3] Around that same year, Holbrook appeared in a television public service announcement (PSA) commissioned by the Ad Council; aimed at the parents of college students planning to study abroad, the PSA sees Holbrook in a jail cell, warning viewers to inform their children of the penalties for drug abuse in countries outside the US.

[21][22] In 1973, Holbrook appeared as Lieutenant Neil Briggs, the boss and rival of Detective "Dirty" Harry Callahan (Clint Eastwood) in Magnum Force, an "obsessively neat and prim fanatic" who supports the obliteration of San Francisco's criminals and who is the leader of a rogue group of vigilante officers.

In 1979, Holbrook starred with Katharine Ross, Barry Bostwick, and Richard Anderson in the made-for-TV movie Murder by Natural Causes.

[27] He appeared in various mini-series, including George Washington (1984), North and South (1985/1986) and Dress Gray (1986), and continued performing in theatrical productions, such as King Lear.

[10] From 1986 to 1989, Holbrook had a recurring role as Reese Watson on Designing Women, opposite his wife Dixie Carter.

[3] Holbrook's film roles during the 1980s and 1990s include a priest in The Fog (1980), a professor in Creepshow (1982), senior stock broker in Wall Street (1987), a neighborly lawyer in Fletch Lives (1989), senior partner of a corrupt law firm in The Firm (1993), and the voice of Amphitryon, the adoptive father of Hercules, in the Disney animated film Hercules (1997).

[31] A year later, Holbrook appeared in Men of Honor, where he portrayed a racist and hypocritical officer who endlessly tries to fail an African-American diver trainee.

[34] He appeared in Sean Penn's critically acclaimed film Into the Wild (2007) and received an Oscar nomination for Best Performance by an Actor in a Supporting Role at the 80th Academy Awards.

[1] At the time, this rendered Holbrook, at age 82, the oldest nominee in Academy Award history in the Best Supporting Actor category.

[1] From late August through mid-September 2007, he starred as the narrator in the Hartford Stage production of Thornton Wilder's Our Town, a role he had once played on television.

That Evening Sun premiered in March 2009 at South By Southwest, where it received the Audience Award for Narrative Feature and a special Jury Prize for Ensemble Cast.

[5] Joe Leydon of Variety hailed Hollbrook's performance in the film as a "career-highlight star turn as an irascible octogenarian farmer who will not go gentle into that good night".

[41] On March 23, 2017, he appeared on an episode on Grey's Anatomy playing a retired thoracic surgeon whose wife is a patient, and on Hawaii Five-0 later in the year.

[29] Holbrook said of his home in McLemoresville, Tennessee, that it had the "feel" of the Mark Twain House in Hartford, Connecticut, and that there was no other place to which he felt so ideally suited.

[10] Holbrook had a recurring role on his wife's hit sitcom Designing Women, appearing in nine episodes between 1986 and 1989 as Carter's on-screen significant other.

[48] He urged others to "move on" from Parker's past and to view the film, which was "an exceptional piece of artistry and a vital portrait of our American experience".