Stethoscopes were originally designed for the auscultation of a patient’s chest for the purpose of listening to lung and heart sounds. These aid medical professionals in their evaluation of the cardiovascular and respiratory systems, as well as in other applications, such as listening to bowel sounds in the gastrointestinal system or assessing for vascular bruits. Listening to internal sounds during chest auscultation aids healthcare professionals in their diagnosis of a patient’s illness. We performed an extensive literature review on the currently available stethoscopes specifically for use in chest auscultation. By understanding the specificities of the different stethoscopes available, healthcare professionals can capitalize on their beneficial features, to serve both clinical and educational purposes. Additionally, the ongoing COVID-19 pandemic has also highlighted the unique application of digital stethoscopes for telemedicine. Thus, the advantages and limitations of digital stethoscopes are reviewed. Lastly, to determine the best available stethoscopes in the healthcare industry, this literature review explored various benchmarking methods that can be used to identify areas of improvement for existing stethoscopes, as well as to serve as a standard for the general comparison of stethoscope quality. The potential use of digital stethoscopes for telemedicine amidst ongoing technological advancements in wearable sensors and modern communication facilities such as 5G are also discussed. Based on the ongoing trend in advancements in wearable technology, telemedicine, and smart hospitals, understanding the benefits and limitations of the digital stethoscope is an essential consideration for potential equipment deployment, especially during the height of the current COVID-19 pandemic and, more importantly, for future healthcare crises when human and resource mobility is restricted.