RENO V. ACLU (1997) ASHCROFT V. ACLU (2004)
Reno v. ACLU and Ashcroft v. ACLU are quintessential First Amendment cases. The federal government deemed a given form of speech socially harmful and took steps to silo it away. In Reno, the Court ruled the Communications Decency Act’s definition of obscenity was too broad and imprecise, censoring an enormous swath of otherwise legal speech, and therefore fell afoul of the First Amendment. In Ashcroft, the Court struck down the Child Online Protection Act as overbroad and ill tailored to its purpose, and therefore also unconstitutional.
In both cases, the ACLU shouldered the burden of making uncomfortable arguments in order to protect free speech, adhered to its higher principles in fighting to protect a core American freedom from overzealous legislators.