It was the last of the James Bond series with Connery as the lead.

Connery won a Best Supporting Actor Academy Award and a Golden Globe for his portrayal of the Irish cop, Malone, in The Untouchables (1987), and was nominated for a Best Supporting Actor Academy Award and a Golden Globe in Indiana Jones and the Last Crusade (1989), playing Jones' father. Connery produced Medicine Man in 1992, and was executive producer and starred in Rising Sun (1993), Just Cause (1995) and The Rock (1996). He also produced and starred in Entrapment (1999), a film that involved him in an on-screen romance with Catherine Zeta-Jones, a woman 40 years younger than Connery. In 2000, he starred in Gus van Sant's Finding Forrester, as a reclusive writer who begins an unusual friendship with a gifted young African-American teenager. Connery was married for 12 years to actress Diane Cilento, between 1962 and 1973. The couple had one son, Jason, born in 1963. His current wife is the French-Moroccan painter, Micheline Roquebrune.

In July 2000, Connery was knighted in his hometown of Edinburgh by Queen Elizabeth II of the United Kingdom.