Theodoor Rombouts was undertook his training in Antwerp, first apprenticed with the little known painter François van Lanckvelt, and then from 1608 possibly with Abraham Janssens. Between 1616 and 1625 he was active in Italy, working in Rome, Pisa and Florence. He became a highly regarded artist and may even have worked for Cosimo II de' Medici, Grand Duke of Tuscany while in Florence.
Rombouts returned to Antwerp by 1625 and became a master of the Guild of Saint Luke. He established a successful career producing mainly secular works for private individuals alongside some altarpieces. Today he is regarded as the key representative of the Flemish Caravaggisti and is best known for his monumental half-length genre scenes executed in a Caravaggesque style. The subjects of these latter works are typical for Caravaggio's followers and include multi-figure compositions of card and backgammon players, musical companies, barber surgeons, as well as smokers and drinkers. His early training under Janssens is also evident in these works, with Rombouts showing his preference for strong three-dimensional qualities and classical shapes.
As the desire for Caravaggesque paintings declined in the 1630s, Rombouts adopted a lighter palette and the use of more diffuse lighting. This change may also have been instigated by an admiration for the late style of Rubens, whom Rombouts assisted in 1635 on the decorations for the Pompa Introitus Ferdinandi.
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