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Wiseguy

Wiseguy

Book by Nicholas PileggiWikipedia

Search complete. 27 mentions across 9 episodes found for "Wiseguy".

Oct 12, 2026

Sarah StefanelliHOST
73:25
... felt a way
Joseph StefanelliHOST
73:26
... is this a better title than Wiseguy?
Sarah StefanelliHOST
73:29
Ah.
Joseph StefanelliHOST
73:29
The book is Wiseguy.
Sarah StefanelliHOST
73:31
Um, I could have been okay with Wiseguy, too.
Joseph StefanelliHOST
73:35
Mm-hmm.
Sarah StefanelliHOST
73:36
Wise Guys.
Sarah StefanelliHOST
73:36
I think that would've been a fine...
speaker_1HOST
38:04
Number one on the list of the most perfect movie adaptations of all time, Martin Scorsese's 1990 masterpiece Goodfellas.
speaker_2HOST
38:12
Based on Nicholas Pileggi's 1985 non-fiction book Wiseguy.
speaker_1HOST
38:17
The article notes that Goodfellas feels uniquely, incredibly cinematic.
speaker_2HOST
38:21
It's pure cinema.
speaker_1HOST
38:22
It is famous for its long tracking shots, its freeze frames, its needle drops.
speaker_1HOST
38:26
But if you read Wiseguy after seeing the movie, it is genuinely eye-opening because the movie is staggeringly in line with the book.
speaker_2HOST
38:34
It's almost verbatim in places.
speaker_1HOST
38:36
Yes.
speaker_5HOST
12:43
A phenomenal book.
speaker_4HOST
12:44
Now, Pileggi had previously written Wiseguy, which Martin Scorsese famously adapted into Goodfellas in 1990.
speaker_5HOST
12:51
Right, a huge cultural touchstone.
speaker_4HOST
12:53
And five years later, they teamed up again for Casino.
speaker_4HOST
12:56
Both books deal with the mob.
speaker_4HOST
12:58
Both are incredibly violent, but the source article draws a really stark contrast between them.
speaker_5HOST
13:03
It does, because while Wiseguy was definitely dark, Casino is significantly more harrowing.
speaker_4HOST
13:09
Why is that, do you think?
Jacob StoopsHOST
63:23
I think he captured his essence.
Jacob StoopsHOST
63:25
There's also many, many stories in the book Wiseguy talking about Tommy's violent tendencies.
Jacob StoopsHOST
63:34
But the question always seems to be... because they come from Henry, are those stories true, factual? So I guess I would ask, before he was killed, where did Tommy fit within the crew? How trusted was he? And was he as violent as they portrayed?
Edward A. McDonaldGUEST
63:54
Yeah.

41 MINS LATER

Edward A. McDonaldGUEST
104:33
And when I was ahead of the strike force and, and, you know, it was somebody who I liked and, uh, I didn't know that he got together with, with, with Henry and they were doing a story, but relatively early on, we're doing a book relatively early on Nick, came and told me what they were doing.
Edward A. McDonaldGUEST
104:49
And I had no control over that, and I more or less allowed them to do it.
Edward A. McDonaldGUEST
104:54
And so 1985, Nick publishes Wiseguy, and it was a bestseller in the New York Times, bestseller list, and a great book, absolutely great book.
Edward A. McDonaldGUEST
105:06
After around the time that the book came out, there was a TV show called Wiseguy, and And there was no connection between them at all.
Jeff NaduHOST
40:51
Tony Soprano, 6653, says, Who is Stanley Diamond? He was an associate of Jimmy Burke, but little is known about him.
Jeff NaduHOST
40:59
His name is mentioned in the book Wiseguy.
Jeff NaduHOST
41:02
Well, this is one question that I did notice when I clicked a thing and actually looked into.
Jeff NaduHOST
41:09
I've actually heard of this guy before.
speaker_1HOST
15:01
And his masterpiece sits at the absolute pinnacle of this ranking.
speaker_1HOST
15:05
Number one on the list of the greatest true crime books ever written is Pileggi's 1985 classic Wiseguy.
speaker_0HOST
15:11
It really is the gold standard of the insider narrative.
speaker_1HOST
15:15
So Wiseguy is the life story of Henry Hill, an associate of the Lucchese crime family in New York, who eventually flips and enters the Witness Protection Program.
speaker_0HOST
15:24
Right.
speaker_0HOST
15:24
Now, the Mafia is notorious for omertà, the code of silence.
speaker_0HOST
15:53
He didn't write him as a tragic Shakespearean antihero.
speaker_0HOST
15:57
He wrote him as a blue-collar worker whose industry just happened to be hijacking, extortion, and eventually narcotics.
Liam O'DonnellHOST
51:47
And it's even like – it's a major sort of theme of the movie, him sort of writing this book, right? That he's like learning how to write and writing a book and the book sort of structures the movie, which is funny because it's based on a character who famously had someone else write the book about him.
Liam O'DonnellHOST
52:03
Am I wrong about that? Did he write – he didn't write Wiseguy, right? Her husband wrote Wiseguy.
Liam O'DonnellHOST
52:08
Her husband wrote it.
Liam O'DonnellHOST
52:08
Yeah, yeah.
Simon WhistlerHOST
0:48
The movie made Henry Hill famous, but there was another important aspect that made this situation unique.
Simon WhistlerHOST
0:54
Goodfellas was based on the book Wiseguy: Life in a Mafia Family, a true crime account by Nicholas Pileggi which chronicled Hill's exploits in the mafia and presented a detailed and ruthless account of the life of a mobster told from a first-hand perspective with the help of Henry Hill himself.
Simon WhistlerHOST
1:09
Unsurprisingly, the book will serve as our main source today as we bring you the story of the man who always wanted to be a gangster in order to become a somebody in a neighborhood full of nobodies.
Simon WhistlerHOST
1:19
[upbeat music] Henry Hill was born on June the 11th, 1943 in Brooklyn, New York, one of eight children to Henry Hill Sr. and Carmela Costa.
ZachGUEST
28:18
As far as Goodfellas, there's just a ton of extra materials for this film, and I had a great time going through them.
ZachGUEST
28:23
So I had read Nicholas Pelleggi's novel Wiseguy a few years ago at this point, and it is written from Pelleggi's perspective about interviewing Hill.
ZachGUEST
28:33
And this is while Henry Hill is still in the Witness Protection Program.
ZachGUEST
28:38
So he's like, they're like sending him to just like random airports and just like making him hop around to like try to like actually get a hold of him.

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