He was in a Buster Keaton short, Pest from the West (1939), then Good Girls Go to Paris (1939) and the serial Overland with Kit Carson (1939).

Craig's big break happened when RKO bought out his contract with Universal to play one of Ginger Rogers' suitors in Kitty Foyle (1940).

[13] RKO gave him the romantic lead in Unexpected Uncle (1941), and he played a New Hampshire farmer who sells his soul in All That Money Can Buy, also titled The Devil and Daniel Webster (1941), with Walter Huston and Edward Arnold.

Louis B. Mayer, head of Metro-Goldwyn-Mayer, thought Craig resembled the studio's most popular male star Clark Gable.

Mayer signed Craig to a seven-year contract to potentially fill in for Gable when he enlisted in the United States Army Air Forces.

[17] He was Ann Sothern's love interest in Swing Shift Maisie (1943) and supported Margaret O'Brien in Lost Angel (1943).

[18] Craig supported Ronald Colman in Kismet (1944), and Lana Turner in Marriage Is a Private Affair (1944); the latter was a big hit.

[16] Craig was given the star role in Gentle Annie (1945) and Dangerous Partners (1945); he was reunited with Margaret O'Brien in Our Vines Have Tender Grapes (1945).

It flopped as did A Lady Without Passport (1950), where Craig supported Lamarr and John Hodiak, and The Strip (1951) with Mickey Rooney.

The Los Angeles Times noted that Craig's MGM contract "seems to go on and on... notwithstanding he only seems to appear in the company's films at well-spaced intervals.

He guest starred on shows like The Millionaire (1956), Broken Arrow (1957), Have Gun – Will Travel as Ralph Coe in S1 E26 "Birds of a Feather" (1958), Colgate Theatre (1958), Death Valley Days (1960), and Tales of Wells Fargo (1962).

He had support roles in Hostile Guns (1967), Fort Utah (1967) and Arizona Bushwhackers (1968) and guest starred in Daniel Boone, Custer, and The Virginian Craig could also be seen in The Devil's Brigade (1968), If He Hollers, Let Him Go!

Both his last film and television performance came in 1972: he played Dr. Hainer in the sci-fi movie Doomsday Machine and John Rodman on The ABC Afternoon Playbreak episode "This Child Is Mine".

[25] In 1963, a judge issued an arrest warrant to Craig for refusing to attend a divorce hearing involving his second wife Jane.

[citation needed] During his 1954 divorce hearing, Craig revealed he made money from a variety of sources in addition to acting, including race horses, a cafe, a chicken ranch, and carpentry.