In the present study, we examined the development of expertise in the careers of three collaborative songwriting teams, Rodgers and Hart, Rodgers and Hammerstein, and George and Ira Gershwin. The primary goal of the study was to extend to collaborative songwriting teams the results of previous research (Hass & Weisberg, 2009), which examined the career development of two seminal composers of American popular music, Irving Berlin and Cole Porter, who wrote both music and lyrics. A quantitative case-study methodology was employed here, using the proportion of hit songs per year within collaborators' active careers as a measure of aesthetic significance (hit ratio). Regression analysis revealed significant positive hit-ratio trends over the careers of the Rodgers-Hart team, and the Gershwin team. In contrast, the Rodgers-Hammerstein team began at a high level of success and exhibited no significant hit-ratio trends. That team began their collaboration when both members were mature professionals, with years of experience writing for Broadway. In addition, both members of the team had collaborated with other individuals earlier in their careers, and both exhibited the expected significant increases in hit ratio with other collaborators prior to their teaming up. Such results are evidence that a process of learning to write hits occurs early in the careers of collaborative songwriting teams, as it does in the careers of composers who both write music and lyrics. Implications of the results and future directions for study are discussed.