Job (dis)continuity and careers configuration are crucial for understanding new and old inequalities on the labour market. The impact of deregulation and flexibilization processes on careers is still unclear. In order to detect vulnerable profiles of workers, it would be useful to analyse the pathways followed by individuals rather than single transitions between different contractual arrangements. The paper focuses on the first eight years of labour market participation. A comparison among four Italian workers’ cohorts is carried out by using the AD-SILC panel, which matches information from the National Social Security’s registers (INPS) and the Italian survey data from the 2005 wave of EU-SILC (European Union Statistics on Income and Living Conditions). First we describe how the features of labour market participation evolve across the cohorts. Second, we highlight the individual characteristics associated with the different career profiles, focussing on the role played by parental background. Finally, we inquire whether different types of trajectories are associated with wage penalties and whether a reproduction of wage inequality through the influence of parental background emerges. The results of the comparison between entry trajectories give support to the hypothesis concerning the high complexity of Italian workers’ careers even for the older cohorts. A certain stability of career profiles exists across cohorts, apart from a reduction of the shares of those leaving the (regular) labour force. This is probably connected to cohort effects and to the increasing female participation to the labour market. Moreover, specific careers and trajectories outcomes are strictly associated with individuals’ socioeconomic characteristics. Even after controlling for the educational level, the entry pathway is connected to the family background. In addition, the early career pattern results in a considerable wage differential (through the different accumulated seniority) for those workers who achieve dependent employment after eight years of labour market participation, hence engendering a permanent penalty for those having followed less stable careers. Finally, the analysis confirms that in Italy coming from a disadvantaged family background negatively affects earnings, even when main outcomes (e.g. education, delay in education, seniority, occupation and sector) are controlled for.