Bobby Hackett, one of nine children, was born and raised in Providence, Rhode Island. At an early age he played the ukulele and by the time he was twelve played guitar and violin, and had bought his first cornet. He left high school after his freshman year to take a steady job with a band that performed seven days a week at the Port Arthur - a local Chinese restaurant. He also played guitar regularly at the Rhodes and Arcadia ballrooms which often broadcasted on Providence radio. A highlight of his time at the Rhodes occurred when the Cab Calloway Band arrived short-handed and invited Bobby to fill in. In the fall of 1932 he was recruited by The Herbie Marsh Orchestra for a winter engagement at a hotel in Syracuse, New York. This was the scene of perhaps the first of many great Hackett anecdotes. Although hired as a guitar player, Bobby preferred the cornet and would play it occasionally. After a few evenings, the manager called Marsh aside and reportedly said "...if that kid picks up the horn again the whole band is fired."
Bobby spent the summer of 1933 on Cape Cod, at the Megansett Tea Room in North Falmouth, playing with Payson Re's band. It was here that he first met Pee Wee Russell. Later in 1933 Russell joined Teddy Roy's band at the Crescent Club, a speakeasy and after-hours place in Boston. Pee Wee then recruited Bobby for the group. In early 1934 Bobby rejoined the Billy Lossez Band at the Biltmore Hotel in Providence, and then traveled to Cape Cod that summer to play in Teddy Roy's quintet at the Megansett Tea Room.
In the fall of 1934, Bobby and Johnny Crandon (a drummer and Harvard Medical School student) formed a band - The Harvard Gold Coast Orchestra - to play New England colleges on weekends. The group consisted of four professional musicians and four medical students. During the next several months the orchestra visited virtually every college between the University of Rhode Island and the University of Maine. In spite of the fact that Bobby was still tied to Providence, he applied for a union card in Boston and received it in early 1935. For the remainder of '35 and early '36 he periodically traveled to Boston from Providence for gigs, typically with Ted Roy.
In mid-1936 Bobby was asked to form a dixieland band to play at The Theatrical Club in Boston, having been recommended by Herbie Marsh who was just finishing an engagement there. To form the group, he took Teddy Roy(p,voc) and Roger Malencourt(b) from the Crescent Club, Russ Isaacs(d) from Meyer Davis's band, and recruited Pat Barbara(cl/alto), Billy Wiles(ts), and Brad Gowans(tb, arr). The Club was an after-hours place and soon became the favorite spot for musicians, both local and out of town visitors. Several reviews of the Hackett band by noted Boston music critic George Frazier drew widespread attention to the group. During the band's one year stay The Theatrical Club grossed more than a million (1937!) dollars.