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The Eighth Amendment has been interpreted to demand proportionality between an offender’s crime and his punishment. However, the current proportionality standard is widely regarded as meaningless. In weighing the severity of the crime against the harshness of the punishment, modern courts do not consider any aspect of the sentence beyond the number of years listed. This Note argues that a more comprehensive analysis of the features of a sentence that contribute to its severity has the potential to reinvigorate the proportionality principle by giving courts a fuller picture of the harshness of modern sentences. Although there are some hurdles to conducting this more robust analysis, this Note proposes methods by which courts could consider the true length of carceral sentences, the prison conditions in which the sentences are served, and the collateral consequences that accompany many criminal convictions. In so doing, this Note demonstrates that some methods of accounting more accurately for the harshness of punishments are neither impracticable nor in tension with other areas of Eighth Amendment doctrine.