With just one film under his belt, Ruddy created “Hogan’s Heroes” (CBS, 1965-1971), a World War II sitcom loosely based on the play “Stalag 17” that depicted the antics of five prisoners of war who are really undercover while trying to subvert the Nazi war effort. When the show’s five year run was over, Ruddy produced his second film, “Making It” (1970), about a sexually triumphant high school student who beds the gerontophobic wife of his gym teacher. After “Little Fauss and Big Halsy” (1970), starring Robert Redford and Lauren Hutton, he produced “The Godfather” (1972) and won his first of two Oscars for Best Picture—presented by future collaborator Clint Eastwood. He had another hit—though not an Oscar winner—with “The Longest Yard” (1974), starring Burt Reynolds as a former football star who leads his fellow inmates in a game against a team of sadistic prison guards. Ruddy then went on to make the controversial “Coonskin” (1975), a mixed live-action and animated fantasy about a black rabbit from the rural south who moves to Harlem and becomes a successful gangster.
Ruddy went on to produce a long string of movies that, in most cases, failed to either make money or please critics, or in some cases both. Though successful at the box office, “The Cannonball Run” (1981) was a wreck of a movie that was bogged down by pointless cameos and listless performances from its two main stars, Reynolds and Dom DeLuise. Following two dismal action flicks, “Death Hunt” (1981) and “Megaforce” (1982), Ruddy returned to produce “Cannonball Run II” (1984), which mimicked its predecessor in artistic quality. Five years later, he returned to the world of illegal cross-country racing a third time with the seemingly disassociated “Speed Zone” (1989), starring John Candy. Thankfully, the movie’s quiet death at the box office marked the end to the dreadful series. Meanwhile, Ruddy moved back into television in 1993 when he created the successful police drama, “Walker, Texas Ranger” (CBS, 1993-2001), starring Chuck Norris as a Texas Ranger who believed in handling criminals the old-fashioned way—by beating them up.
While “Walker, Texas Ranger” did well on television, Ruddy continued producing films, but with similar results as before. “Ladybugs” (1992), “The Scout” (1994), “Bad Girls” (1994) and “Heaven’s Prisoners” (1996) were all forgettable additions to his resume. With “Mean Machine” (2002), Ruddy tried to relive the success of “The Longest Yard”—only this time the game was soccer—but middling reviews and a low flight path on the box office radar hindered his ambitions. Then out of the blue, Ruddy struck gold with “Million Dollar Baby” (2004), directed by Clint Eastwood. Co-starring Hilary Swank and Morgan Freeman, Eastwood played Frankie Dunn, an old-school boxing trainer afraid of intimacy after a painful rift with his daughter (Eastwood claimed the raspy voice he adopted for the role was inspired by Ruddy's distinctive vocals). Praised by a majority of critics as an exquisite and subtle film, “Million Dollar Baby” received wide acclaim and won several awards, including a second Best Picture Oscar for Ruddy. Meanwhile, the producer was set to release the remake to “The Longest Yard”, this time starring Adam Sandler and Chris Rock.
Because of their social connections within the Hollywood community, Ruddy's wife Wanda McDaniel helped the fashion designer Giorgio Armani make major inroads within the Industry, serving as an entertainment outreach coordinator to help dress the celebrities in Armani's chic formal wear.