Osgood was also known for being the narrator of Horton Hears a Who!, an animated film released in 2008, based on the book of the same name by Dr. Seuss.

He often played piano between records on his shows and frequently collaborated with other students, including future actor Alan Alda and future producer and director Jack Haley, Jr.[8] Immediately after graduating from Fordham University, Osgood was hired as an announcer by WGMS (AM) and WGMS-FM, the classical music stations in Washington, D.C. (today WWRC and WTOP-FM respectively).

Senator Everett Dirksen (R- Illinois), they shared a Grammy Award for best spoken word performance for their single Gallant Men.

[11] As Dirksen read a patriotic poem written by H. Paul Jeffers about the dignity of duty in the armed forces, it was framed by Cacavas and Osgood's martial music and stirring choral refrains.

"[15] In September 1955, President Dwight D. Eisenhower suffered a serious heart attack during a vacation in Denver, Colorado, and was confined to a hospital room there until November.

During this time, under the auspices of WGMS, Osgood hosted a closed-circuit program of classical music delivered exclusively to the president's room to encourage his relaxation and convalescence.

[16] When his tour with the U.S. Army Band was completed, in October 1957, Osgood returned to WGMS full-time as announcer Charles Wood and as a special assistant to the general manager.

[18] In 1960, credited by name and as a WGMS announcer, he provided introductions and commentary on a six-record album of a collection of thirty-three speeches by President Franklin Delano Roosevelt titled FDR Speaks.

[22] Although RKO expected to operate WHCT at a loss for the three years before the Federal Communications Commission was due to renew the station's license, by early 1963, the financial realities became too difficult to bear unabated.

[23] In a 1985 interview with Broadcasting magazine, Osgood explained: [The station] lost money at an alarming rate ... [RKO] let me off the hook very gently.

"[15]Unemployed at age 30, Osgood turned to one of his Fordham classmates, Frank McGuire, who directed program development at ABC in New York.

In 1963, McGuire hired Osgood to be one of the writers and hosts of Flair Reports, which related human interest stories on the ABC Radio Network.

[30] Each three-minute Osgood File focused on a single story, ranging from a breaking development of national importance to a whimsical human-interest vignette.

[32][33] Among Osgood's personal trademarks were his bow tie,[34] his weekly TV signoff "Until then, I'll see you on the radio",[35] and his propensity for delivering his commentaries in whimsical verse.

[6] When they became empty nesters, Osgood and his wife moved to a 12-room duplex on West 57th Street at 7th Avenue in New York City.

[3][40] CBS News Sunday Morning dedicated its full January 28, 2024, broadcast to celebrating Osgood's life and work.