# Sinatra as Dirty Harry? **URL:** \ **Category:** Cafe Society\ **Created:** [January 7, 2020, 9:42am UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062 "2020-01-07T09:42:00Z")\ **Posts on this page:** 20\ **Page:** 1
**Author:** ![bionic\_man](https://avatars.discourse-cdn.com/v4/letter/b/49beb7/32.png) [@bionic\_man](https://boards.straightdope.com/u/bionic_man)\ **Post date:** [January 7, 2020, 9:42am UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/1 "2020-01-07T09:42:00Z")
Orgriginaly Old blue eyes was going to play dirty harry.do you think th is would of worked? ---
**Author:** ![Banksiaman](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/banksiaman/32/3334_2.png) [@Banksiaman](https://boards.straightdope.com/u/Banksiaman)\ **Post date:** [January 7, 2020, 9:51am UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/2 "2020-01-07T09:51:26Z")
Cranky Harry? Frankly, no. While I enjoyed Sinatra in Manchurian Candidate and other stuff and have no problems with him as an actor, I think Clint gave Harry Callaghan an easy physicality. He’d already built his reputation through the spaghetti westerns and brought parts of that taciturn delivery, toughness and slightly mystical prescience to Dirt Harry. While Sinatra would have just done it differently, I’m not sure it would not have become an iconic character, and a multi-movie saga. ---
**Author:** ![Chefguy](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/chefguy/32/138_2.png) [@Chefguy](https://boards.straightdope.com/u/Chefguy)\ **Post date:** [January 7, 2020, 3:09pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/3 "2020-01-07T15:09:23Z")
Sinatra was 56 years old when that movie was made, and he was already starting to look jowly and soft by then. Eastwood was 41 and in good physical shape. As a rogue cop with a bad attitude, he was perfect. Sinatra was more of the smooth operator type in that genre of films. It wouldn’t have worked nearly as well. ---
**Author:** ![BrotherCadfael](https://avatars.discourse-cdn.com/v4/letter/b/977dab/32.png) [@BrotherCadfael](https://boards.straightdope.com/u/BrotherCadfael)\ **Post date:** [January 7, 2020, 3:14pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/4 "2020-01-07T15:14:10Z")
Ten years earlier? Maybe. ---
**Author:** ![Dendarii\_Dame](https://avatars.discourse-cdn.com/v4/letter/d/bbce88/32.png) [@Dendarii\_Dame](https://boards.straightdope.com/u/Dendarii_Dame)\ **Post date:** [January 7, 2020, 4:10pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/5 "2020-01-07T16:10:40Z")
In a related anecdote, Bing Crosby was offered the part of Columbo, but turned it down. [Columbo - Wikipedia](https://en.wikipedia.org/wiki/Columbo) ---
**Author:** ![puddleglum](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/puddleglum/32/137_2.png) [@puddleglum](https://boards.straightdope.com/u/puddleglum)\ **Post date:** [January 7, 2020, 4:31pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/6 "2020-01-07T16:31:51Z")
John Wayne, Robert Mitchum, Burt Lancaster, George C Scott, Robert Mitchum, and Paul Newman also passed on the role. Most because the movie was considered right wing and too filled with violence. ---
**Author:** ![dasmoocher](https://avatars.discourse-cdn.com/v4/letter/d/dbc845/32.png) [@dasmoocher](https://boards.straightdope.com/u/dasmoocher)\ **Post date:** [January 7, 2020, 5:41pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/7 "2020-01-07T17:41:25Z")
> [@puddleglum](#): > > John Wayne, Robert Mitchum, Burt Lancaster, George C Scott, Robert Mitchum, and Paul Newman also passed on the role. Most because the movie was considered right wing and too filled with violence. Too right-wing for John Wayne? Although I could see Wayne objecting to a cop who breaks the rules like torturing the suspect (stepping on his wound in the Keyser Stadium scene). By chance I recently saw a clip of Kirk Douglas on the Dick Cavett show talking about working with Wayne, he basically said they were good friends but never talked politics. ---
**Author:** ![bionic\_man](https://avatars.discourse-cdn.com/v4/letter/b/49beb7/32.png) [@bionic\_man](https://boards.straightdope.com/u/bionic_man)\ **Post date:** [January 7, 2020, 8:47pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/8 "2020-01-07T20:47:34Z")
John Wayne appeared in a copy cat dirty harry film.in the 70s ---
**Author:** ![Bryan\_Ekers](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/bryan_ekers/32/183_2.png) [@Bryan\_Ekers](https://boards.straightdope.com/u/Bryan_Ekers)\ **Post date:** [January 7, 2020, 9:05pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/9 "2020-01-07T21:05:32Z")
> [@bionic\_man](#): > > John Wayne appeared in a copy cat dirty harry film.in the 70s You mean _Brannigan_ ? [Here’s a clip of him of him asking Baldrick if he feels lucky.](https://www.youtube.com/watch?v=31nbTYePtaY) Well… asking a pre-_Blackadder_ Tony Robinson if he can swim, but same thing. ---
**Author:** ![Hypno-Toad](https://avatars.discourse-cdn.com/v4/letter/h/b2d939/32.png) [@Hypno-Toad](https://boards.straightdope.com/u/Hypno-Toad)\ **Post date:** [January 7, 2020, 9:25pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/10 "2020-01-07T21:25:06Z")
Was that also Richard Bucket (Boo-kay) in that clip? ---
**Author:** ![Chefguy](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/chefguy/32/138_2.png) [@Chefguy](https://boards.straightdope.com/u/Chefguy)\ **Post date:** [January 7, 2020, 9:49pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/11 "2020-01-07T21:49:58Z")
> [@puddleglum](#): > > John Wayne, Robert Mitchum, Burt Lancaster, George C Scott, Robert Mitchum, and Paul Newman also passed on the role. Most because the movie was considered right wing and too filled with violence. Of those, I could only see Mitchum pulling it off. ---
**Author:** ![bonzer](https://avatars.discourse-cdn.com/v4/letter/b/45deac/32.png) [@bonzer](https://boards.straightdope.com/u/bonzer)\ **Post date:** [January 7, 2020, 11:44pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/12 "2020-01-07T23:44:35Z")
> [@Hypno-Toad](#): > > Was that also Richard Bucket (Boo-kay) in that clip? Nope - Richard Attenborough. ---
**Author:** ![Smapti](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/smapti/32/17938_2.png) [@Smapti](https://boards.straightdope.com/u/Smapti)\ **Post date:** [January 8, 2020, 11:31am UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/13 "2020-01-08T11:31:23Z")
Well, we _did_ kinda-sorta get [Sinatra as John McClane.](https://en.wikipedia.org/wiki/The_Detective_(1968_film)) ---
**Author:** ![Dale\_Sams](https://avatars.discourse-cdn.com/v4/letter/d/779978/32.png) [@Dale\_Sams](https://boards.straightdope.com/u/Dale_Sams)\ **Post date:** [January 8, 2020, 2:26pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/14 "2020-01-08T14:26:58Z")
> [@Smapti](#): > > Well, we _did_ kinda-sorta get [Sinatra as John McClane.](https://en.wikipedia.org/wiki/The_Detective_(1968_film)) I was going to say…Sinatra could have made Dirty Harry work. ---
**Author:** ![Wendell\_Wagner](https://avatars.discourse-cdn.com/v4/letter/w/8491ac/32.png) [@Wendell\_Wagner](https://boards.straightdope.com/u/Wendell_Wagner)\ **Post date:** [January 8, 2020, 2:55pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/15 "2020-01-08T14:55:49Z")
I’ve talked about the John McClane films before, so let me just repeat what I said. These movies were cobbled together from spare parts. _The Detective_ was a 1968 film made from a 1966 novel of the same name. By the time the sequel (_Nothing Lasts Forever_) to the novel came out in 1979, Frank Sinatra was too old really to play the lead again. The script made from that novel bounced around Hollywood for years. Finally they decided to change the main character’s name, change some things in the plot, make no reference to the film _The Detective_, and rename the film _Die Hard_. It finally came out in 1988 with Bruce Willis in the lead and was a major hit. Then the filmmakers took another script that had been bouncing around Hollywood for a while which was based on a novel called _58 Minutes_ by a different novelist that had no relationship to the first film. They changed things in the plot and made Bruce Willis’s character the lead in the new film, which was called _Die Hard 2_ when it came out in 1990. It was again a big hit. They then took another script that had been bouncing around Hollywood for a while called _Simon Says_ with no relation to the first two John McClane films. They again rewrote this in the same way as the first two films into a 1995 film called _Die Hard with a Vengeance_, and it was once more a big hit. They then took another script that had been bouncing around Hollywood called _[WW3.com](http://WW3.com)_ and again rewrote it as a John McClane film. It came out in 2007 and was called _Live Free or Die Hard_ and was, yes, you guessed it, a hit. They then had someone write an original script for the next movie. The new film came out in 2013 and was called _A Good Day to Die Hard_. This film, the only one in the series which had a script originally written to be a John McClane film, is sometimes considered the poorest one in the series. ---
**Author:** ![NDP](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/ndp/32/55_2.png) [@NDP](https://boards.straightdope.com/u/NDP)\ **Post date:** [January 8, 2020, 6:26pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/16 "2020-01-08T18:26:35Z")
> [@Dale\_Sams](#): > > I was going to say…Sinatra could have made Dirty Harry work. He might have but it would’ve changed the movie’s story considerably. Instead of a cowboy cop bucking the system and bending the rules to clean up the streets it would be about an aging veteran police detective who can’t adjust to the changes in law enforcement and society in general in the post-_Miranda_ era. ---
**Author:** ![puddleglum](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/puddleglum/32/137_2.png) [@puddleglum](https://boards.straightdope.com/u/puddleglum)\ **Post date:** [January 8, 2020, 6:35pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/17 "2020-01-08T18:35:59Z")
> [@bionic\_man](#): > > John Wayne appeared in a copy cat dirty harry film.in the 70s The John Wayne casting is disputed by IMDB but he appeared in two knockoffs, McQ and Brannigan. ---
**Author:** ![Dale\_Sams](https://avatars.discourse-cdn.com/v4/letter/d/779978/32.png) [@Dale\_Sams](https://boards.straightdope.com/u/Dale_Sams)\ **Post date:** [January 8, 2020, 10:18pm UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/18 "2020-01-08T22:18:29Z")
> [@NDP](#): > > He might have but it would’ve changed the movie’s story considerably. Instead of a cowboy cop bucking the system and bending the rules to clean up the streets it would be about an aging veteran police detective who can’t adjust to the changes in law enforcement and society in general in the post-_Miranda_ era. Damn good assessment Similarly Walter Matthau makes “Charley Varrick” work. Even if he didn’t understand it ---
**Author:** ![fedman](https://avatars.discourse-cdn.com/v4/letter/f/278dde/32.png) [@fedman](https://boards.straightdope.com/u/fedman)\ **Post date:** [January 10, 2020, 1:39am UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/19 "2020-01-10T01:39:31Z")
if Sinatra sounds unwise, how about Ian Fleming wanting David Niven as 007? ---
**Author:** ![LH75](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/lh75/32/4438_2.png) [@LH75](https://boards.straightdope.com/u/LH75)\ **Post date:** [January 10, 2020, 1:58am UTC](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062/20 "2020-01-10T01:58:55Z")
The man who introduced “Some Like it Hot” on TCM last night said that Frank SInatra was the first choice for Daphne, played by Jack Lemmon. The movie would have tanked. [Next page](https://boards.straightdope.com/t/sinatra-as-dirty-harry/846062.md?page=2)