The first volume of Going Hollywood presented 46 selections from Bing Crosby's first 13 feature films; the second volume contains 50 tracks from his next ten. As a successful recording artist in addition to being a movie star, Crosby generally went into the recording studio just before one of his films was to open and recorded versions of some or all of the songs he sang in the movie. In the first volume of Going Hollywood, compiler Geoff Milne relied primarily on these non-soundtrack recordings, originally released on Brunswick and Decca Records, including only 11 actual soundtrack performances when there were no equivalent studio recordings. In the second volume, he includes more actual soundtrack material, even when Crosby made Decca versions of the tracks, but he still uses 24 studio recordings, among them the number one hit renditions of "Pennies From Heaven," "Sweet Leilani," and "The Moon Got in My Eyes." (Though Milne offers no explanations for his choices, one can assume that sound quality and the nature of the soundtrack versions affected his decisions. In some cases, Crosby sang a song only in part in a film, while his studio version was complete.) Some films, such as Pennies From Heaven, are represented entirely by studio recordings, others, such as The Star Maker, primarily by soundtrack recordings.
The soundtrack material tends to be more interesting than the more familiar studio tracks, especially since it often features guest performers. Ethel Merman duets with Crosby on "You're the Top" and "Shanghai-De-Ho" from Anything Goes; Martha Raye is heard on "I'm an Old Cowhand" from Rhythm on the Range and "After You" from Double or Nothing; and other notable vocalists include Louis Prima, the Sons of the Pioneers (with the future Roy Rogers), Beatrice Lillie, and a very young Donald O'Connor. Crosby himself, in his mid-thirties at the time, is in good form, rescuing quite a few mediocre songs and getting the best out of standards like "You're the Top," "I'm an Old Cowhand," "Pennies From Heaven," "Blue Hawaii" (done in a dialogue scene with Shirley Ross from Waikiki Wedding), and "Small Fry." The album includes a couple of rarities in "The House Jack Built for Jill," cut from Rhythm on the Range after the scene was shot, and "Where Is Central Park?," cut from Sing You Sinners after only the initial prerecording had been made. "An Apple for Teacher" from The Star Maker is missing, because, Milne claims, Crosby's singing is drowned out by a children's chorus in the film (he also made a studio recording), though the real reason is probably a lack of space on this two-CD set that runs over 144 minutes.