Streptococcus pneumoniae is an infrequent cause of infectious endocarditis in adults. In the past 2 years, however, we have encountered several cases at our institution, and additional cases have been reported in the literature. This infection typically follows pneumonia in the setting of chronic alcoholism and may additionally be complicated by meningitis. Less commonly, pneumococcal endocarditis occurs in other hosts or follows primary infection at other extrapulmonary sites. In such cases, the diagnosis may be initially missed, with a resultant delay in institution of appropriate therapy. Moreover, there are controversies regarding the optimal therapy for infections of this nature in the era of penicillin resistance. Since a comprehensive review of this topic has not been published since 1990, we reviewed cases of pneumococcal endocarditis in the penicillin era, with particular attention to disease recognition, the role of echocardiography, and the dilemmas surrounding medical and surgical therapeutic interventions.