Kalugin's guitar mastery combines classical and rock guitar trends, his music covers such different genres as progressive rock, Baroque music, flamenco; his poetics deals with such themes as Hermeticism, Kabbalah, vampirism, Christian esoterism, Gnosticism, Buddhism etc.,[2] and also includes some satirical component.

However, Kalugin's dissatisfaction with his manner of playing grew; he was greatly impressed by the achievements of both his friend and competitor, Yuri Naumov, who has since been widely considered one of the best Russian acoustic rock guitarists.

A year later he released his first successful album Nigredo featuring flamboyant complex lyrics and music, the latter unusual for both Russian bard and acoustic rock as it had been before.

foundation run by an association of well-known Moscow-based rock musicians named Sergey Kalugin Russia's Best Acoustic Guitarist 1994.

[11] In 2012 Sergey Kalugin expressed his support of Pussy Riot[12] during the criminal prosecution of the Russian activist punk band.