Graduated from Boris Yukhananov's Studio of Individual Directing (MIR-2). In productions by Boris Yukhananov he has played the roles of Petya Trofimov in The Garden (1990-2002), Treplev in The Seagull (1993-1999), Mephistopheles and Faust in Faust (1999-2003). He was a participant of the Edinburgh International Theatre Festival in 1995 and the World Theatre Olympics in Moscow in 2001.
He has been one of the organizers of the CINE FANTOM Film Club since 1997.
That same year he made a short film called Emma Tsunts, based on a story by Jorge Luis Borges. The film was screened as a competition entry at the Hamburg International Film Festival in 1998, and a year later was shown at the Stuttgart Festival. Since 1999 he has worked as a director and producer on the STS, TNT, and MTV television channels. He participated in the rebranding of the TV channels Zvezda, STS, and Domashny (Silver Promax UK 2005, London). In 2011, as a director and creative producer, he created a series for the First Channel: Choose a Fate in which Alexander Gordon played the lead role. In 2012 he directed the film The Dream of an Oligarch, based on the novel by Yury Mamleev. This film was screened at the 34th Moscow International Film Festival, and received the Grand Prix of the 15th Pure Dreams – Deboshirfilm international film festival.
He was a nominee for the Innovation Award in the All-Russian Competition in the Field of Contemporary Visual Arts (2010).
Dobrovolsky directed Friedrich Dürrenmatt’s The Visit at the Stanislavsky Electrotheatre. It was his debut in the dramatic theatre.