Distracted driving (driving while performing a secondary task) causes many collisions. Most research on distracted driving has focused on operating a cell-phone, but distracted driving can include eating while driving, conversing with passengers or listening to music or audiobooks. Although the research has focused on the deleterious effects of distraction, there may be situations where distraction improves driving performance. Fatigue and boredom are also associated with collision risk and it is possible that secondary tasks can help alleviate the effects of fatigue and boredom. Furthermore, it has been found that individuals with high levels of executive functioning as measured by the OSPAN (Operation Span) task show better driving while multitasking. In this study, licensed drivers were tested in a driving simulator (a car body surrounded by screens) that simulated simple or complex roads. Road complexity was manipulated by increasing traffic, scenery, and the number of curves in the drive. Participants either drove, or drove while listening to an audiobook. Driving performance was measured in terms of braking response time to hazards (HRT): the time required to brake in response to pedestrians or vehicles that suddenly emerged from the periphery into the path of the vehicle, speed, standard deviation of speed, standard deviation of lateral position (SDLP). Overall, braking times to hazards were higher on the complex drive than the simple one, though the effects of secondary tasks such as audiobooks were especially deleterious on the complex drive. In contrast, on the simple drive, driving while listening to an audiobook lead to faster HRT. We found evidence that individuals with high OSPAN scores had faster HRTs when listening to an audiobook. These results suggest that there are environmental and individual factors behind difference in the allocation of attention while listening to audiobooks while driving.