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

We debated for a long time about whether to write about the following video, which comes from a murder trial in which a man named Caleb Flynn is accused of killing his wife. The crime is very serious, and very sad, and yet the following video demonstrates something about where we are as a society. 

The trial has received national attention and has been streaming live. Toward the end of the proceedings Thursday, the prosecution played two versions of an AI love song that Flynn, a former American Idol contestant, generated for his mistress. Investigators found the AI song files as well as lyrics for the song in Flynn’s Notes app after using the forensic tool GrayKey to break into his phone. 

“We found audio files on Caleb’s iPhone that seem to have been AI generated and related to his relationship with [his mistress],” Joseph Wilhelm, a forensic investigator testified. “They’re in two different keys. One’s like a happy or upbeat sad song if that makes any sense, and one’s a sad, sad song. I think one’s in a minor key, one’s in a major key, but I’m not a music professional.” 

“Permission to publish, your honor?,” the prosecutor says. 

“You may,” the judge says.

What follows feels like it should be from an I Think You Should Leave skit or a Nathan Fielder bit. It is real, however. Everyone in the court spends the next few minutes trying not to laugh during what is, again, a murder trial. It simply must be seen to be believed:

When the songs mercifully end, the court goes silent for several seconds. The judge then says: “We’re going to break for the day. It’s 10 after 4 [p.m.] We will reconvene tomorrow.”  

Earlier in the day, Flynn’s mistress was asked to read various text messages he wrote her into the public testimony. “I’ve spent a lot of time on my own and in Cleveland. I finished the lyrics to our song. To your song. Although it may mean nothing to you, I wanted to give them to you. I have the music which is completely different to what you’ve heard to this point and I was going to record it but I know there will be no way I would ever be able to actually sing it again,” Flynn wrote. 

“Do you want to hear the song I wrote for you with an AI voiceover,” Flynn also wrote. “I have this software called ElevenLabs where I loaded the song on piano and sent it with my computer microphone to which I can pick an AI voice to sing it better.”

“I don’t know if I’m ready to listen to this yet. I’m sorry,” she responded. “Send me the song and I’ll save it to my phone and I’ll listen when I’m ready, even if it’s a month from now. I don’t want it to be erased.”

“Are you sure? It messed up the outro as it’s supposed to be done and the vocals aren’t exactly how I want it, it was a little rock-ier at times but the melody is correct. I tried to sing it with passion and AI took it and went a little extreme.”

“It’s OK,” she said. 

The investigation into the murder is actually 404 Media-relevant for several reasons. The AI-generated songs were found after Wilhelm used both Cellebrite and Graykey to try to break into Wilhelm’s phone. 

Ultimately Wilhelm used Graykey’s Magnet tool to unlock and examine Flynn’s phone, which gave him a “full file system extraction.” Wilhelm then obtained Flynn’s messages, the AI audio files, cell phone location history, sleep data from Flynn’s Oura Ring, heart rate data from an Apple Watch, learned that Flynn deleted an app called “AI music song generator” days before the murder, and AirPod connection and disconnection information.