Asymmetry in the allocation of information, together with personal and market conditions, may lead to an inequality of bargaining power between contracting parties. In other words, in the context of contract formation, one party may enjoy a superior bargaining position on the other, which may be exploited in the form of unfair contractual terms and misleading conduct. Different legal regimes have developed their own remedies to protect the weaker contractual party, more generally consumers, in such scenarios. The aim of this paper is to confront U.S. and Italian legal rules, in terms of effectiveness and efficacy in accomplishing this goal. This work will try to address differences and analogies between these legal systems, aiming to ascertain their ability both to foster freedom of contract and offer consumer protection at the same time. The work will present an introductory part, which will define what is meant by “inequality of bargaining position“ and “vices of consent” in the contractual setting, followed by two other main sections. The first section will introduce the “doctrine of unconscionability”, by evidencing those aspects which distinguish it from classical contractual remedies. Subsequently, attention will focus on Italian legal provisions of standard terms and contracts, and consumer protection. Together with the Italian Civil Code provisions, contents and aims of the European Directive 13/93 on “unfair terms in consumer contracts” will be briefly considered. The second part will provide a comparative analysis between of the Italian and the U.S. provisions, where differences and analogies between the two legal systems will be underpinned. The aim is to tackle the legal tendencies which have been developed in the Italian context with the consolidated practices of U.S. law. The results of this comparative analysis will offer some conclusions on the efficacy of the Italian legal norm, in an attempt to provide a cross-country overview of legal remedies against oppressive clauses and other forms of unequal bargaining.