We study the kinematics and dynamics of a highly compliant membrane disk placed head-on in a uniform flow. With increasing flow velocity, the membrane deforms nonlinearly into increasingly parachutelike shapes. These aerodynamically elongated materials exhibit a modified drag law, which is linked to the elastohydrodynamic interactions. We predict the unsteady structural response of the membranes using a nonlinear, aeroelastic model-in excellent agreement with experimental measurements of deformations and force fluctuations. With simultaneous membrane interface tracking, force measurements and flow tracing, we reveal that a peculiar skewness in the membrane's oscillations triggers turbulence production in the wake, thereby modulating the drag. The present work provides a demonstration of the complex interplay between soft materials and fluid turbulence, leading to new, emergent system properties.