1999–2005: Breakthrough in Russia, Philosophy of Miracle and Songs of My Mother
After being rejected from a musical college in his native Odesa, his family did not have the money to send him to a private institution. As a result, Vitas, already using the name as a pseudonym, started performing at night clubs. He initially started his career as a Michael Jackson tribute act, but also performed parodies and his own songs. He also sold leftover bread from stores on the street as well as offering his services as a photographer. At night clubs, he had acts involving dancing, singing, comedy and magic tricks, including spoon bending. He worked as an actor in an experimental theatre. He applied to perform with his own songs at the 1997 edition of Chervona ruta festival, but was rejected as his repertoire lacked songs in Ukrainian. In 1999, Odesan regional television station Elan shot a music video for his song "Opera #1", which they recorded in Odesa.
During one of his night club performances, where he performed "Opera #2", he was spotted by a Russian producer who recommended that he move to Moscow, which he had already considered in 1998–1999. During a play at the experimental theatre, he was spotted by producer Sergey Pudovkin, whom he gifted a cassette of his song. A week later, Vitas and Svetlana left Odesa.
With Pudovkin, Vitas starting working on his debut for the Russian audience. He started working for youth channel TV-6. They recorded a music video for "Opera #2", in which Vitas portrayed an eccentric lonely man with fish gills who lives in a bathtub with jars of fish and plays the accordion naked. The music video premiered in December 2000 and received wide public attention. Vitas started performing the song with artificial gills, which let the Russian media compare him to Ichthyander, a character in the novel Amphibian Man.
On February 27, 2001, Vitas premiered his solo concert show "Opera #...", in an abridged form, at the "Russia" Concert Hall in Moscow. Performed as a teaser for the first leg of his "Philosophy of Miracle" tour, the show was filmed by TV-6 and later broadcast as part of the music program "Наша музыка". Although not well documented, official sources recall that the tour began on April 7, 2001, presumably in Naro-Fominsk. Other sources confirm that the tour had already started by March 2001. During that first tour, Vitas performed not only in concert halls, but also on TV shows, festivals, stadiums, casino halls and nightclubs. In March 2002, Vitas made his first tour in the United States of America.
On March 29, 2002, Vitas premiered the second leg of his "Philosophy of Miracle" concert tour with a concert at the State Kremlin Palace in Moscow. The concert was filmed by Channel One Russia and later released on DVD.
In late 2002, Vitas received an invitation from Lucio Dalla, the composer of "Caruso", to perform this song together with him at the "Sanremo in Moscow" concert in the State Kremlin Palace on November 23, 2002. Mr. Dalla then invited Vitas to come to Rome to take part in the rehearsals of Toska, a modern version of Puccini's opera.
In dedication to his mother who died in 2001, Vitas released two albums: "Mama" and "The Songs of My Mother". The latter included classic Soviet songs which were the favourite of Vitas' late mother. During the process of recording the album, Vitas befriended Soviet and Russian composer Alexandra Pakhmutova, who featured in his music video for her song "The Bird of Happiness".
On October 21, 2003, Vitas ended his first concert tour "Philosophy of Miracle" with its last gig in Kaliningrad.
On November 1, 2003, Vitas presented his second concert tour with the show "The Songs of My Mother" in the "Russia" Concert Hall in Moscow. Compared to the flamboyant nature of his previous Philosophy of Miracle tour, The Songs of My Mother was more conservative, drawing on classic Russian songs. From 2004 to 2006, Vitas' management, the "Pudovkin" Production Center continued "The Songs of My Mother" tour in Russia and the United States, Germany, Kazakhstan, Israel and the Baltic states.
In addition to his singing career, Vitas also starred in a murder mystery television series called "Сволочь ненаглядная" ("Beloved Scoundrel"), in which he played a pop singer with an unusually high voice. He also starred in a comedy called Crazy Day.