No doubt one of Van Gogh's most macabre works, Skull with Burning Cigarette is probably the most distinguished of his paintings from the Antwerp period.
It's likely that the work was painted from a skeleton in an anatomy class while Vincent was studying art. A sketch, Hanging Skeleton and Cat, from the same period would appear to confirm this. The work--a stark momento mori--was produced in a time when Van Gogh's health was poor (due to stomach ailments and rotting teeth) and may reflect Vincent's own concerns about his state of well-being. Some interpret the work as being a statement of defiance against Vincent's faltering health.
This disturbing painting may have been influenced by the similar macabre works produced by the Belgian artist Félicien Rops. It's known that Vincent owned a copy of Rops' Uilenspiegel, a satirical arts journal and the work of Rops (shown at right), The Husbands' Train: The Death of the Sinner, suggests a clear influence on Vincent's own two skull and skeleton works cited here.
Van Gogh may also have been influenced by one of his own countrymen, the 17th century Dutch artist, Hercules Segers, who also produced a disturbing work of a skull. It remains uncertain whether Van Gogh was aware of Segers' works, but he did, of course, have a thorough knowledge of Dutch painters throughout the 17th to 19th centuries.