Helst's first known picture, “Four Regents of the Walenweeshuis” (1637; Amsterdam, Walenweeshuis Orphanage), is closely related to the work of Nicolaes Eliasz., who was possibly his master. Success came rapidly to Helst, bringing influential sitters and important commissions to him at an early age. In 1642 he painted the Amsterdam burgomaster Andries Bicker and his wife and son, and in 1643 he completed a great portrait group, “The Company of Captain Roelof Bicker and Lieutenant Blaeuw,” which formed part of the same scheme of decoration as Rembrandt's “Nightwatch.” Helst replaced Rembrandt as Amsterdam's most fashionable portrait painter in the mid-1640s. His facile portraits reflect the courtly and elegant manner that came to be preferred in Dutch painting from that time.