Still, Aladdin resisted releasing the remaining material from the Sha-Weez's J&M session, nor did the label book another studio date. The group nevertheless remained under contract to the label, but in late 1953 Crawford and Myles began recording for Chess as Sugar Boy and His Cane Cutters. Their Chess debut, "I Don't Know What I'll Do," was the label's first release cut in New Orleans, and enjoyed strong local airplay. The follow-up, "Jock-a-Mo," appeared in early 1954 and also proved a regional favorite. A decade later, the Dixie Cups recut the song as "Iko Iko," one of the most popular and enduring Crescent City R&B records ever made (although Crawford claimed he never earned a dime for co-writing the tune). The third Sugar Boy and His Cane Cutters single, "I Bowed on My Knees," earned the group a residency at the Baton Rouge nightspot the Carousel Club, but brought an end to their Chess affiliation, leaving more than a dozen unreleased sides on the shelf; Myles left the lineup in 1955 to join Li'l Millet & His Creoles, and Crawford dissolved the Cane Cutters soon after in favor of a solo career.

In 1956 Crawford signed to Imperial, reuniting with Bartholomew and his ace session band of saxophonists Lee Allen and Herb Hardesty, guitarist Justin Adams, bassist Frank Fields, and drummer Earl Palmer. With his solo debut, "She's Got a Wobble (When She Walks)," Crawford clearly set out to cross over to white radio, and while he did indeed earn airplay on stations on both sides of New Orleans' color line, his efforts failed to translate into record sales. Both "I Don't Need You" and "She's the One" followed in 1957, but when 1958's "I Need Your Love" again tallied dismal sales, Imperial terminated his contract. By 1962, Crawford was working with the Little Raelettes, the quartet of singers Dianne and Linda DeGruy, Irene Williams, and Mary Kelly; during their debut performance, the group was erroneously introdced as Sugar Boy and the Sugar Lumps, and the name stuck. But while en route to their first Peacock label session in 1963, Crawford was pulled over by a policeman and pistol-whipped, missing the studio date and enduring a protracted hospital stay that largely soured his desire to continue performing. After an abortive 1969 comeback attempt, Crawford confined his singing to the church until 1995, when he lent backing vocals to grandson Davell Crawford's debut LP, Let Them Talk.