Devil-May-Care was created at the end of August 1999 by Elf (Real Name: Ilya; ex-Gothic Sky; vocals/keyboards) and Scum (Real Name: Pavel; guitar). Later that year, Diesel (Real Name: Mikhail; bass) joined them. The group was finally formed in the autumn of 2000 when the final two members of Spawn (Real Name: Stas; ex-Erich Zaan; guitar) and Helen (Real Name: Elena; vocals) came together. The drums were computer programmed.
The group had its debut in Michurinsk at Metalfest-2001 festival. Soon after, in July 2001 at Scum Records' and S&I studios' Awe was recorded in March 2002.
In November 2002, Devil-May-Care took part in Tambovski Volk Festival. In January 2003, the line-up of the group changed when Scum was replaced by Witch Grinder (Real Name: Àlexandr; ex-Astral Gates; guitars). Awe, released by Russian independent label Stygian Crypt Productions', was characterized by Melodic Black Metal featuring specifically Classical, Celtic Folk melodies and traditional of European Gothic.