Often cast as a piano player, Winebold has starred in the television shows On the Case with Paula Zahn and Celebrity Ghost Stories, and in the films The Letter and Vengeance.

[2] Native to Pine City, New York, Winebold practiced musical theater in Ireland, Japan, and Korea before returning home.

[10] He was selected as musical director for the 2010 revival of The Irish… and How They Got That Way Off-Broadway,[11] restaged to honor the one-year anniversary of playwright Frank McCourt's death on July 19.

[18] Winebold portrayed street singer and pianist Rusk Greene in the Great Depression retrospective Southern Crossroads at the Totem Pole Playhouse in Fayetteville, Pennsylvania, in August 2011,[19][20] and was music director for Little Women at Long Island's Secret Theatre in December 2011.

[22] He returned to the Interlakes Theatre to direct music there for Always, Patsy Cline, November 19–20, 2011, and reprised the show at the Concord City Auditorium, April 21–22, 2012.

[35] Winebold starred in "The Final Act", an episode of Investigation Discovery's documentary Fatal Encounters portraying Charles Yukl, a musical director and piano bar player, regarded as a sociopath.

[37] For the eighth season of On the Case with Paula Zahn in 2013, he starred as Chris Lang in "Nine Days of Terror"[38] and Gerald Powers in "A Fateful Decision".

[39] His other appearances include the shows Celebrity Ghost Stories[40] and Funny or Die Presents, as well as TV commercials for Canon Inc. and other brands.

[50] In addition to acting and musical direction, Winebold currently serves as accompanist and vocal coach in New York City,[1] and aspires to play in a Broadway orchestra pit.

[40] Winebold's direction of The Irish… and How They Got That Way was reviewed positively as providing "comic flair" during "No Irish Need Apply"[9] and "a rich tapestry of song and speech".