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Greenway's first appearances were uncredited in two 1949 films, ''Impact'' and ''Deputy Marshal.'' Often he was cast as a law enforcement officer. He was an unnamed townsman in the 1952 Dale Robertson (1922-2013)  film based on Bret Harte's [[short story]], "The Outcasts of Poker Flat." <ref name=imdb/> Greenway later appeared in many well known films including ''North by Northwest,'' ''High Noon,'' ''How the West Was Won,'' ''Peyton Place,'' and ''Who Wants to Marry a Millionaire?''<ref name=imdb/>​

Greenway's first appearances were uncredited in two 1949 films, ''Impact'' and ''Deputy Marshal.'' Often he was cast as a law enforcement officer. He was an unnamed townsman in the 1952 Dale Robertson (1922-2013)  film based on Bret Harte's [[short story]], "The Outcasts of Poker Flat." <ref name=imdb/> Greenway later appeared in many well known films including ''North by Northwest,'' ''High Noon,'' ''How the West Was Won,'' ''Peyton Place,'' and ''Who Wants to Marry a Millionaire?''<ref name=imdb/>​

Greenway appeared twice in 1954-1955 on the Rod Cameron syndicated television series, ''City Detective.'' In 1955, he guest starred in the episode "The Big Genius" of [[NBC]]'s ''[[Dragnet]],'' starring and narrated by Jack Webb. In 1958, Greenway appeared four times on Rod Cameron's second syndicated series, ''State Trooper,' western set in the 1950s.. He portrayed Sheriff Bronson in the episodes "Stay Lost, Little Girl," "Dangerous Honeymoon," "Full Circle," and "Death on Wheels.'' In 1957, Greenway was cast in the episode "Copper Wire" of another syndicated crime drama, ''Sheriff of Cochise'', set in [[Arizona]]  in 1958, he portrayed Deputy Sheriff Tom Munger in the episode "Sentenced to Death" of Bromfield's successor series, ''U.S. Marshal.''<ref name=imdb/>

Greenway appeared twice in 1954-1955 on the Rod Cameron syndicated television series, ''City Detective.'' In 1955, he guest starred in the episode "The Big Genius" of [[NBC]]'s ''[[Dragnet]],'' starring and narrated by Jack Webb. In 1958, Greenway appeared four times on Rod Cameron's second syndicated series, ''State Trooper,'' western set in the 1950s. He portrayed Sheriff Bronson in the episodes "Stay Lost, Little Girl," "Dangerous Honeymoon," "Full Circle," and "Death on Wheels.'' In 1957, Greenway was cast in the episode "Copper Wire" of another syndicated crime drama, ''Sheriff of Cochise'', set in [[Arizona]]  in 1958, he portrayed Deputy Sheriff Tom Munger in the episode "Sentenced to Death" of Bromfield's successor series, ''U.S. Marshal.''<ref name=imdb/>

In 1958, he appeared as Kylie in the episode entitled "Geronimo," of Pat Conway ''Tombstone Territory,'' also set in Arizona. John Doucette was cast in the same episode as the [[Apache]] Chief Geronimo. Greenway appeared in 1958 as Dr. Quinn in "The Dan Hogan Story" of the NBC western series, ''Wagon Train.'' Another appearance in 1958 was as Lt. Peters in the episode "Double Jeopardy" of the [[CBS]] crime drama, ''Richard Diamond, Private Detective,'' starring David Janssen as a private investigator]]. In 1959, he portrayed John Sebrey in "Death of a Gunfighter" on Richard Boone's CBS western series, ''Have Gun - Will Travel].'' That same year, he played the role of rancher Frank Chanault in the film ''These Thousand Hills.''<ref name=imdb/>

In 1958, he appeared as Kylie in the episode entitled "Geronimo," of Pat Conway ''Tombstone Territory,'' also set in Arizona. John Doucette was cast in the same episode as the [[Apache]] Chief Geronimo. Greenway appeared in 1958 as Dr. Quinn in "The Dan Hogan Story" of the NBC western series, ''Wagon Train.'' Another appearance in 1958 was as Lt. Peters in the episode "Double Jeopardy" of the [[CBS]] crime drama, ''Richard Diamond, Private Detective,'' starring David Janssen as a private investigator]]. In 1959, he portrayed John Sebrey in "Death of a Gunfighter" on Richard Boone's CBS western series, ''Have Gun - Will Travel].'' That same year, he played the role of rancher Frank Chanault in the film ''These Thousand Hills.''<ref name=imdb/>