Drowsiness and fatigue are major safety issues that cannot be measured directly. Their measurements are sustained on indirect parameters such as the effects on driving performance, changes in physiological states, and subjective measures. We divided this study into two distinct lines. First, we wanted to find if any driver’s physiological characteristic, habit, or recent event could interfere with the results. Second, we aimed to analyze the effects of subjective sleepiness on driving behavior. On driving simulator experiments, the driver information and driving performance were collected, and responses to the Karolinska Sleepiness Scale (KSS) were compared with these parameters. The results showed that drowsiness increases when the driver has suffered a recent stress situation, has taken medication, or has slept fewer hours. An increasing driving time is also a strong factor in drowsiness development. On the other hand, robustness, smoking habits, being older, and being a man were revealed to be factors that make the participant less prone to getting drowsy. From another point of view, the speed and lane departures increased with the sleepiness feeling. Subjective drowsiness has a great correlation to drivers’ personal aspects and the driving behavior. In addition, the KSS shows a great potential to be used as a predictor of drowsiness.