Meet Jaymes Osborne

Jaymes Osborne is a multifaceted performer and educator whose passion for the arts spans the worlds of musical theatre, dance, and vocal performance. A singer, actor, and dancer from Chicago, IL, Jaymes has appeared in acclaimed regional productions including Rent, Hairspray, Dessa Rose, Avenue Q, The Color Purple, and Jesus Christ Superstar. His performances have earned multiple Jefferson Award nominations and wins, celebrating his versatility and commitment to storytelling on stage. In addition to his professional stage work, Jaymes is an experienced teaching artist and choreographer, having led classes in beginner tap, hip-hop, and modern dance for students ranging from kindergarten through high school. He has choreographed and directed productions such as Grease, Smokey Joe’s Café, The Wedding Singer, and Hairspray, fostering creativity, confidence, and collaboration in young performers. Jaymes brings his background as a lead vocalist, ensemble artist, and musician—skilled in guitar, piano, and drums—into every classroom setting, blending professional insight with an infectious enthusiasm for performance. Dedicated to inspiring the next generation of artists, Jaymes believes in using the performing arts as a powerful tool for expression, discipline, and community connection. He is extremely excited to experience the growth set forth by PTPT.