The present series of three independent studies examines how workaholism and work engagement combine relying on a variety of distinct methodologies: interaction effects (Study 1, n = 160), a person-centered approach (Study 2, including two samples of n = 321 and 332), and a hybrid mixture regression approach (Study 3, n = 283). This research also documents the relations between workaholism, work engagement, and work outcomes (i.e., work-family conflicts, work performance, sleeping difficulties, and burnout). Furthermore, this research investigates the role of workload (Studies 2 and 3) and perceived social support (Study 2) in the prediction of profile membership. Studies 1 and 2 showed that the combination of high levels of work engagement with high levels of workaholism was associated with a variety of negative outcomes. In Study 3, the highest levels of sleeping difficulties and work-family conflicts were associated with the workaholic profile, followed by the engaged-workaholic profile, and finally the engaged profile. Finally, in Studies 2 and 3, workload showed strong associations with an increased likelihood of membership into the profiles characterized by higher levels of workaholism.