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Spektor was born in Moscow, Russia, Soviet Union to a musical family. Her father, a photographer, was also an amateur violinist, and her mother was a music professor in a Russian conservatory; she now teaches at a public elementary school in Mount Vernon, New York. Her surname, Spektor, is derived from the Russian.
Spektor studied classical piano from the age of six, and was also exposed to the music of rock and roll bands such as The Beatles, Queen, and The Moody Blues by her father, who obtained such recordings in Eastern Europe and traded cassettes with friends in the Soviet Union. The family left the Soviet Union in 1989, when Regina was nine, during the period of Perestroika when Jewish citizens were permitted to emigrate, traveling first to Austria and then Italy, they finally settled in the Bronx, New York.
Since roughly 2005, Spektor has performed on a bright red Baldwin baby grand piano. She opened for The Strokes in 2003, on her first North American tour. Subsequently, she appeared on Late Night with Conan O'Brien twice, The Tonight Show with Jay Leno twice, Jimmy Kimmel Live, and Last Call with Carson Daly twice. She has toured the United States and Europe. Although she generally only performs original material, she performed her first covers in 2005, of songs by Leonard Cohen and Madonna for the 2nd Annual Jewish Music & Heritage Festival in New York City.
While with The Strokes on their 2003/2004 Room on Fire tour, Spektor performed "Modern Girls & Old Fashion Men" alongside the band.
In 2006, Spektor embarked on a successful headlining tour of the United States and Europe, selling out numerous clubs and theaters.
In New York, Spektor gained a firm grounding in classical music from her piano teacher, Sonia Vargas, a professor at the Manhattan School of Music. Although she had always made up songs around the house, Spektor first became interested in songwriting during a visit to Israel with the Nesiya Institute in her teenage years. Attracting attention from the other children on the trip for the songs she made up while hiking, she realized she had an aptitude for songwriting. Following this trip, she was first exposed to the work of Joni Mitchell, Ani DiFranco, and other singer-songwriters, which gave her the idea that she could create her own songs.
Spektor completed the four-year studio composition program of the Conservatory of Music at Purchase College in Purchase, New York within three years, graduating with honors in 2001. She worked briefly at a butterfly farm in Luck, Wisconsin. She gradually achieved recognition through performances in the anti-folk scene in downtown New York City, most importantly at the East Village's Sidewalk Cafe. During this period, she sold her self-produced CDs 11:11 and Songs at such performances.