Articular cartilage was predicted to be one of the first tissues that could successfully be regenerated, but this proved not to be the case. In contrast, bone but also vasculature and cardiac tissues have seen numerous successful reparative approaches, despite consisting of multiple cell and tissue types and thus possessing more complex design requirements. Here, we use bone regeneration successes to highlight cartilage regeneration challenges, namely selecting appropriate cell sources and scaffolds, creating biomechanically suitable tissues, and integrating to native tissue. Also discussed are technologies addressing hurdles of engineering a tissue possessing mechanical properties unmatched in man-made materials and functioning in environments unfavorable to neotissue growth.