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1958年，伊利诺斯州Joliet监狱，Nathan Leopold第五次面对假释委员会。他终于说出了三十五年前把他送进监狱的“世纪犯罪”的事实（唱段：WHY）。这一次，为了获得释放他揭露出比以往任何一次更多的内幕。在他的记忆中，事情要追溯到1924年的芝加哥，当时他还是一个19岁的男孩。他和Richard Loeb是一对分享友谊，性爱和一些轻微犯罪行为的同窗好友。夏天结束后他们即将进入不同的法学院而面临分离，Nathan急切渴求Richard保持两人的关系，而Richard却表现得漫不经心（唱段：Everybody Wants Richard）。Richard引诱Nathan参与他今晚要实施的一起对废弃仓库的纵火，Nathan只得屈从（唱段：Nothing Like a Fire）。
第二天，Nathan恳求Richard停止犯罪活动，而Richard却只一味贪婪地阅读尼采的书籍，并提议两人签署一份书面合同（唱段：A Written Contract），内容包括Richard将满足Nathan一切情欲方面的需求，但条件是Nathan必须协助他完成一些微不足道的小犯罪。Nathan虽然很不情愿，但还是答应了。他们以血签下契约，开始持续尝试各种各样的犯罪活动，直到Richard厌倦了这些不痛不痒的小罪行，开始谋划一场超级犯罪，他想要杀死自己的弟弟John，但遭到Nathan的反对。Nathan指责Richard没有好好履行协议，Richard为了得到Nathan的帮助做出了妥协，并满足了Nathan的欲望（唱段：Thrill Me）。Richard最终决定进行一场无差别谋杀和虚假的赎金交易，对象是一个素不相识的男孩（唱段：The Plan）。Richard坚称，凭借他们的智慧和细致的策划，绝不会被警方查到蛛丝马迹。为了不触怒Richard，Nathan别无选择，只能同意。
场景回到1958年的Joliet假释委员会，Nathan回忆起案发当时矛盾复杂的感受（唱段：Way Too Far）。Richard准备了谋杀器具：绳子，撬棍和硫酸。Richard诱使受害者坐上他的跑车后实施了谋杀（唱段：Roadster）。清理犯罪现场时，Richard颂赞着超级犯罪的美德（唱段：Superior），令Nathan不寒而栗。回家后，他们继续实施赎金计划（唱段：Ransom Note），但意想不到的是尽管他们已精心部署，发现尸体的报导还是于第二天见诸报端。随后Nathan丢失的眼镜又被发现在犯罪现场附近。Nathan恐慌地给Richard打电话，Richard在电话里竭力安抚他（唱段：My Glasses/Just Lay Low）。当警方最终通过眼镜追查到Nathan，Richard帮助他编造紧急托辞和教练他如何应对警察的盘问（唱段：I'm Trying to Think）。
但当Nathan顺利应付了警察之后，Richard提出了分手，理由是为了确保自己未来律师的仕途。他将一切责任推卸在Nathan遗落了眼镜的错误上。Nathan感觉遭到了Richard的背叛，于是与检察官达成交易，供出主犯Richard以此来换取减刑。
被捕后，Richard发现没有其它出路，于是再次用自己的魅力诱惑Nathan，说服他放弃和检察官的交易，和他一起分担罪行，接受同样的惩罚（唱段：Keep Your Deal With Me）。在等待宣判的牢房里，Richard的喃喃自语被Nathan听到，原来他外表虽然始终表现得很强劲，内心却非常害怕被判死刑（唱段：Afraid）。最终由于他们的律师Clarence Darrow的狡猾策略，他们逃脱死刑，被判监禁。
在监狱里，Nathan终于揭示了自己那令人震惊的计划：因为害怕失去Richard，他参与了谋杀，但在谋杀的整个过程中他都事先留下线索，甚至故意把眼镜遗落在现场，他知道只有这样才能确保Richard和他永远在一起，或者至少是（唱段：Life Plus 99 Years）。
如今整个真相终于大白，在Richard和Nathan的这场角逐中，最终的胜利属于Nathan，但这样的胜利却又是苦乐参半，因为Nathan在服刑35年后获得假释，而Richard却已在几年前被监狱里的犯人所杀，离开监狱后Nathan必须独自面对外面的世界（唱段：Finale）。。。。。。
It is 1958 at Joliet Prison, Illinois, where Nathan “Babe” Leopold faces the Parole Board for the fifth time. He tells them the facts of the “crime of the century” that sent him to prison thirty-five years earlier ("Why"). But this time he reveals more than ever, hoping it will lead to his release. In his memory, he goes back to 1924 Chicago, where, as a nineteen year old boy, he anxiously meets up with Richard Loeb, a classmate with whom he has shared friendship, sex and participation in minor crimes. Richard, who has been away at college, treats Nathan indifferently. Nathan begs to renew their relationship before separating again after the summer to attend different law schools ("Everybody Wants Richard"). Richard relents and allows Nathan to join in his activity for the evening – setting an abandoned warehouse on fire. In front of the blaze ("Nothing Like a Fire"), which arouses Richard, Nathan finally gets what he wants.
The next day, Nathan implores Richard, who is voraciously reading Nietzsche, to stop the criminal activity. Instead Richard, now empowered by the theory of the Superman, threatens to drop Nathan completely unless they create "A Written Contract" detailing that Richard will satisfy Nathan’s sexual needs only in exchange for Nathan’s expertise as his accomplice in petty crimes. Reluctantly, Nathan agrees. They sign in blood and their crime spree continues until Richard fails to live up to his end of the agreement ("Thrill Me"). Richard explains that he is bored with the misdemeanors and wants to commit a “superior” crime: the murder of a young boy ("The Plan") and a phony ransom scheme after the killing. Richard insists that their intellect and meticulous plotting will prevent them from being caught. Nathan has no choice but to agree or risk Richard’s wrath.
Back in 1958 at Joliet before the Parole Board, Nathan explains his feelings ("Way Too Far") as he recalls how Richard prepared the murder weapons and supplies: rope, a crowbar and a bottle of acid. Richard lures the victim by promising a ride in his "Roadster". While cleaning up the murder scene, Richard extols the virtues of being "Superior" to a shaken Nathan. Back at Richard’s house they compose the bogus "Ransom Note" and proceed with their plans. The next day, the newspapers reveal that, despite their careful planning, the body has been found. As a few more days go by, Nathan’s missing eye-glasses are discovered near the scene of the crime. While Nathan panics, Richard tries to calm him ("My Glasses/Just Lay Low") over the phone. When the glasses are eventually traced to Nathan, Richard helps him concoct an emergency alibi and coaches him in how to answer the cops ("I'm Trying to Think"). After Nathan is successful with the police, Richard declares their relationship over so he can protect his future as a lawyer. He reminds Nathan that everything would have been fine if the glasses hadn’t been dropped. Feeling betrayed, Nathan cuts a deal with prosecutors, turning in Richard in exchange for a lighter sentence.
When arrested, Richard realizes there is no way out and works his charms on Nathan ("Keep Your Deal With Me") by convincing him to give up the deal and accept the same punishment. While awaiting the penalty trail in his jail cell, Richard doesn't realize Nathan can hear him muttering to himself that he is truly "Afraid" despite his strong façade. Thanks to the cunning strategies of their lawyer, Clarence Darrow, they escape the death penalty and are sentenced to prison. Behind bars, Nathan finally reveals his own shocking plan: fearing the loss of Richard, he went along with the murder but stayed one step ahead the entire time, even deliberately planting his glasses, knowing that all this would ensure his desire to be together forever, or at least for "Life Plus 99 Years". Now that the whole truth has finally been exposed, back at Joliet prison Nathan is granted parole. It is a bittersweet victory; since Richard was murdered by another inmate years before, Nathan must face the outside world alone ("Finale").