Elliott and Goulding began on Boston radio. Each was a disc jockey with his own program on radio station WHDH-AM, and each would visit with the other while on the air. Their informal banter was so appealing that WHDH would call on them, as a team, to fill in when Red Sox baseball broadcasts were rained out. Elliott and Goulding (not yet known as Bob and Ray) would improvise comedy routines all afternoon, and joke around with studio musicians.

Elliott and Goulding's brand of humor caught on, and WHDH gave them their own weekday show in 1946. Matinee with Bob and Ray was originally a 15-minute show, soon expanding to half an hour. This is why Elliott and Goulding became known as Bob and Ray: it rhymed with "Matinee." Goulding later quipped, "If the word had been Matinob, we would have been Ray and Bob."

Elliott and Goulding lent their voices to a variety of recurring characters and countless one-shots. Those played by Elliott included Wally Ballou, an inept news reporter whose opening transmission was invariably cut off (" lly Ballou here" snappy sportscaster Biff Burns ("This is Biff Burns saying this is Biff Burns saying goodnight" Tex Blaisdell, a drawling cowboy singer who also did rope tricks on the radio; Arthur Sturdley, an Arthur Godfrey take-off; Johnny Braddock, another sportscaster, with an obnoxious streak; and a host of others. In addition, any script calling for a child's voice would usually go to Elliott.

Goulding played mushmouthed book reviewer Webley Webster (who was also an "actor," portraying Calvin Hoogavin on one of Bob and Ray's soap opera parodies farm editor Dean Archer Armstead (his low, slurring delivery was unintelligible and punctuated by the sound of his spittle hitting a cuspidor Charles the Poet, who recited soppy verse (parodying the lugubrious late night broadcaster Franklyn MacCormack) but could never get through a whole example of his bathetic work without breaking down in laughter; serial characters such as Matt Neffer, Boy Spot-Welder; crack-voiced cub reporter Arthur Schrank, and all female roles. While originally employing a falsetto, Goulding generally used the same flat voice for all of his women characters perhaps the most memorable of these was Mary Margaret McGoon (satirizing home-economics expert Mary Margaret McBride), who offered bizarre recipes for such entrees as "ginger ale salad" and "mock turkey." In 1949, Goulding, as Mary, recorded "I'd Like to Be a Cow in Switzerland", which soon became a novelty hit and is still occasionally played by the likes of Dr. Demento. On radio, Goulding also played the females in the various soap opera spoofs, but for the television series, first Audrey Meadows and then Cloris Leachman appeared on camera in these roles (usually either Mary Backstayge or Linda Lovely).

This collection of Bob and Ray Greats includes 244 different shows and appearances for a total of 83+ hours of listening enjoyment.

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