Transcript for 20.5: Dear Leon 3

[Ambient noises and jazz drones and play throughout fade up. Someone handwriting a letter. A typewriter. A computer. The typewriter jumps to a new line, producing a DING noise. Drone music crescendos and then fades quickly. “Drive the Cold Winter Away” fades up].


Dear Leon,

Still no answer to my previous letters. It’s okay, I’m not sure I deserve one. I have been a really bad Ben Affleck lately. Like…(sighs)…like ‘Gigli’ bad.  

You know, I think about Ben Affleck sometimes. The — the “real” Ben Affleck, not the bad Ben Affleck I’ve become. I think about his career after Good Will Hunting and how hard it must have been for him watching his goody-goody buddy Matt Damon blow up. Matt Damon who won all those Oscars for playing all the Kennedy’s in that big Kennedy biopic. Matt Damon, the Bourne Supremacy, Ultimatum, Paramountcy, then The Bourne Loser, and finally Bourne Again. Matt Damon, who became a water charity champion, who made knit-your-own tux’s cool again. Matt Damon, one of Ocean’s trusted 11.

And there’s Ben Affleck trying to make it for himself in Reindeer Games. Phantoms. The Jersey Devil. Payment, Payback, Paycheck. And then the Toilet Ring Kids remake. I guess some people liked Armageddon. Not my cup of tea, but that’s not the point. Armageddon was the high point for Ben Affleck. After that, nothing but bombs and before long he ends up starring in that movie where the poor dude who played Superman kills himself.

Ben Affleck must have not known what to do with himself, you know? Which way to go. He was trying too hard to be Matt Damon. I realize that now. He must have trusted his agent, and his directors, and all these other people who promised they knew what was best for him, promised him that if he starred in that movie as a US president who declares nuclear war on Ecuador, he’d be up there with Matt Damon again. Ben Affleck believed in them and felt these people gave him some sense of purpose. Trying so hard to be someone he wasn’t made him feel lost, so he listened to anyone he could and did whatever they said until he lost himself even more. Next thing you know, Gigli is unleashed upon the world.

But that’s why there’s hope for Ben Affleck. You see, he eventually forgot about trying to be Matt Damon. What he really wanted to do was direct.

[Drive the Cold Winter Away slowly fades out].

So he starts making these movies on his own, and you know what? He’s really good. His first movie gets a lot of critical attention. And soon, Ben Affleck directs a movie he also stars in, and it wins him a ton of Oscars. He’s on top again and it’s all because he figured out who he was. He trusted in himself. He became self-reliant, self-sufficient. He stopped listening to others about what to do and started listening to himself about what to do.

[Farewell to Nigg begins to play]

That’s not the end, though. Ben Affleck is still capable of making mistakes, he’s always going to be on a bit of thin ice. After that big Oscar win, he directed that movie about William Henry Harrison, the president that died of pneumonia thirty days after he was sworn in? He gave a super long inauguration speech in the rain and then got really sick. Ben Affleck filmed Harrison’s entire presidency in real time. Not a good move at all. I think…I think he was interested in investigating a complete picture of failure and alienation because he could relate. He also starred in that movie where Batman kills Superman in the end. I think that was because he was thinking about his past, you know? Thinking about where he was at his lowest, playing the dude who played Superman who felt like he failed so much, and who got so lost he…he ended up…well, you know.

The point is, there is still hope for Ben Affleck and I guess what I’m saying is, in order to be more like Matt Damon? The goody-goody Matt Damon we’re constantly comparing ourselves to, the one who seems so hopelessly out of reach? We just have to step out of his shadow and embrace the Ben Affleck’s we really are. We have to direct ourselves. We have to take that bad Ben Affleck who is ordering us what to do and ordering us how to do it and get him gone, baby. Gone.  


Olive in Gardener


Greater Boston is written and produced by Alexander Danner and Jeff Van Dreason with recording and technical assistance from Marc Harmon.

You can help Greater Boston to reach new listeners by leaving us a rating and review on iTunes.

This mini-episode featured:

  • Kelly McCabe as Nica Stamatis (she/her)

Drive the Cold Winter Away and Farewell to Nigg performed by Adrienne Howard, Emily Peterson and Dirk Tiede. Some sound effects and music used from public domain and creative commons sources.

Episode transcripts will be posted online at

[Farewell to Nigg fades out].

Content Warnings

  • References to historic suicide
  • References to nuclear war
  • References to Gigli
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