AI Love Song for Mistress Played at Murder Trial Is Most Excruciating Watch in Recent Memory

A murder trial in which Caleb Flynn is accused of killing his wife took a bizarre turn Thursday when prosecutors played two AI-made love songs he had generated for his mistress. The case has drawn national attention and has been streamed live, but even by that standard, this was an especially hard thing to watch.

Investigators said they found the songs and lyrics in Flynn’s Notes app after using GrayKey to get into his phone. Forensic investigator Joseph Wilhelm told the court the audio files appeared to be AI-generated and tied to Flynn’s relationship with the woman. He described the two versions as having different keys, one sounding more upbeat and sad, the other more plainly sad, though he was careful to add he was not a music professional.

Before the songs were played, the mistress was asked to read messages Flynn had sent her aloud in public testimony. In those texts, Flynn wrote that he had finished the lyrics to “our song,” said he had music that was different from what she had heard before, and explained that he used software called ElevenLabs after loading the song on piano and sending it from his computer microphone. He also said he had tried to sing it himself, but AI had made it “a little extreme.”

The songs were awkward enough that the court seemed to freeze in place while they played. When they finally ended, there was silence for several seconds. Then the judge called a break and said the court would reconvene the next day.

The technical side of the investigation was just as revealing as the music was embarrassing. Wilhelm said he used Cellebrite and GrayKey in an effort to break into Flynn’s phone, and GrayKey’s Magnet tool ultimately gave him a full file system extraction. From there, investigators pulled Flynn’s messages, the AI audio files, cell phone location history, sleep data from his Oura Ring, heart rate data from his Apple Watch, and signs that he deleted an app called “AI music song generator” days before the murder. They also found AirPod connection and disconnection records.