The effect of insoluble surfactants on drop deformation and breakup in simple shear flow is studied using a combination of a three-dimensional boundary-integral method and a finite-volume method to solve the coupled fluid dynamics and surfactant transport problem over the evolving interface. The interfacial tension depends nonlinearly on the surfactant concentration, and is described by the equation of state for the Langmuir isotherm. Results are presented over the entire range of the viscosity's ratio; and the Surface coverage x, as well as the capillary number Ca that spans from that for small deformation to values that are beyond the critical one Ca-cr. The values of the elasticity number E, which reflects the sensitivity of the interfacial tension to the maximum surfactant concentration, are chosen in the interval 0.1 <= E <= 0.4 and a convection dominated regime of surfactant transport, where the influence of the surfactant on drop deformation is the most significant, is considered. Fora better understanding of the processes involved, the effect of surfactants on the drop dynamics is decoupled into three surfactant related mechanisms (dilution, Marangoni stress and stretching) and their influence is separately investigated. The dependence of the critical capillary number Ca-cr(lambda) on the surface coverage is obtained and the boundaries between different modes of breakup (tip-streaming and drop fragmentation) in the (lambda;x) plane are searched for. The numerical results indicate that at low capillary number, even with a trace amount of surfactant, the interface is immobilized. which has also been observed by previous studies. In addition. it is shown that for large Peclet numbers the use of the small deformation theory to measure the interfacial tension in the case where surfactants are present can introduce a significant error. (c) 2005 Elsevier Inc. All rights reserved.