A Countdown of the 25 Greatest Gambling Movies of All Time: #21 -- "29th Street"

Other Nov 16, 2020

This is a daily countdown of the greatest gambling movies of all time ranked from #25 to #1.  Today, we feature #21 – "29th Street," released in 1991.

29th Street is a mostly-forgotten movie gem carried by standout performances that may best be described as a cross between Goodfella's and It's a Wonderful Life.

When released back in 1991, it was overshadowed by a number of blockbuster films of this same genre (Goodfella's, Godfather Part III, A Bronx Tale, Bugsy), but it’s still worth seeing.

We meet the stereotypical New York Italian-immigrant family doing all the usual goombah things – from simmering Sunday sauces in the kitchen to flirting with Mafia goons to using the F-word as a perfunctory adjective at every social gathering.  However, 29th Street is actually the (based on a) true story of the real first-ever New York State Lottery winner and the final days leading up to his $6.2 million dollar payday.  New York State legalized the state lottery in 1976, and there was a popular frenzy surrounding that first drawing.  

Guess who wins, but then feels like the worst person on earth?  With that, the story begins.

Frank Pesce, a character actor who appeared in many similar films, wrote the screenplay.  His lead character of the same name is played by the very underrated actor Anthony LaPaglia.  But 29th Street's anchor is the late great Danny Aiello (who died earlier this year), playing Frank Pesce, Sr., who turns in one of his best performances at the top of his game.

As for the plot, imagine winning millions in the lottery, and then being sick about it.  That's where the story begins, told in flashbacks.  Again, think of Goodfella's at Christmas, decorated with F-bombs.

Yeah, the topic is the lottery, which isn't really gambling.  But it sorta' is.  So, we'll include this among our Top 25 greatest gambling movies.

The Pointspreads.ca Top-25 Countdown (with Links):

#22 – Oceans Eleven (2003)

#23 – Molly's Game (2017)

#24 – Owning Mahowny (2003)

#25 – The Killing (1956)

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