Ep 116: Showtime's City on a Hill Creator, Chuck MacLean:  How to Make it in Hollywood Even if You're a "Sh*tbum from Quincy"

At 33 years old, Chuck MacLean has worked with some of the biggest talents in Hollywood like Brad Pitt and Antoine Fuqua.  Currently, he collaborates with major players Ben Affleck, Matt Damon, Tom Fontana, Jennifer Todd and Kevin Bacon with his critically-acclaimed Boston Cop Drama, City on a Hill.  What I enjoyed most in sitting down with him is his ability to say it like it is without worrying what others will think of him.  Sure, it might warrant an "explicit" rating (F-bombs abound), but you'll feel like you're back on the streets of Boston with this self-described "shitbum from Quincy" who pulled off "the biggest con of all" by hitting it big in Hollywood as a screenwriter.  If he can go from being bloody and chased by cops to creating a major hit in under 15 years, maybe you can too.  His "no" stories may just be funnier, and more dangerous, than yours! 



Wanting to write male-driven dramas but learning early on that no one wanted them unless they were placed within a genre film, (4:55). The culture shock moving from Boston to LA, (6:18). "It was thing where I realized, 'oh, to really make a successful story, you just need to care about the characters and the story can be kind of secondary.  Even if you're using a basic genre element, a basic genre structure... if the character's good, no one's really paying attention to that," (7:57). The whole City on a Hill story, starts with that movie 'Black Mass', (9:29). The joys of working with Ben Affleck as a producer, (11:05).  Being hired by for his particular voice by Ben Affleck, (13:50).  The best moment of Chuck's career, at Ben Affleck's house, (15:43).  The surreal quality of success in Hollywood coupled with the blunt truth of how hard the work is, (17:21). The best advice I got early on was that it doesn't cost anybody anything to call you a genius", (18:17). The effortless beauty of Kevin Dunn's acting, (19:22). The influence of Chuck's grandfather on his desire to be a writer, (21:59).  Story about doing grandfather’s eulogy, (23:28).  The responsibility of writing because he knew his parents were broke, (27:00).  Being terrible at everything else and falling back on writing, (27:24).  Chuck’s college experience, (30:04).  "The only thing that made me happy was getting myself out of trouble", (35:15).  Using people’s doubt as fuel, (37:24).  Realizing that normal people don’t get drunk on Friday nights and get into fights and how that freed up much more time to pursue a dream, (39:44). Chuck’s daily writing routine, (44:13). How Chuck approaches fictional stories, (46:55).  "So, like, if I'm gonna go write a cop show about Boston, right?  What does the audience expect that to look like? ...  'okay, well how do I come in from the left then?  And hit them sideways?'" (50:23). The pragmatic, almost mathematical problem-solving aspects of screenwriting, (52:21). “I usually do it based on whatever I’m going through, ‘cause that’s what I’m gonna be interested in writing about”, (54:52). Chucks massive body of work, including short stories, (55:34). “10% of my job is actually writing... 90% of it is just dealing with bullshit”, (1:00:28).  "Big time agent read it, guy's been around forever... he flipped out.  He sent it to an editor and that guy flipped out... they were so excited about the whole thing, and then... nothing ever happened.  It got shot down everywhere," (1:02:23).  Chuck’s “Sicilian” take on how the brain works, (1:08:09). “That’s what I would say to that kid, “believe it or not, it’s gonna work out kinda the way you think it is,”(1:20:14). Bonus Hollywood horror stories, (1:21:14). 


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IMDB: Chuck MacLean Film / TV Credits

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The Godwulf Manuscript (Wikipedia)IMDB: David Lowery (IV) Film / TV Credits



Ep 53: Emmy-Award Winner Richard Schiff, of The West Wing & The Good Doctor

Ep 47:  Goliath Showrunner, Lawrence Trilling

Ep 61:  Elite Hollywood Producer, Jennifer Todd

Ep 104:  City on a Hill Actor, Mark O'Brien


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Matthew Del Negro