Anybody want to help me answer this letter?

If they're up for something subtitled, there's Tony Takitani.

Lars and the Real Girl. Just don't tell them ANYTHING about it beforehand.

Reign Over Me.

I guess that, if I were grieving, seeing a film where someone else is grieving may not be a help, unless that film were a documentary. But that's just me.

Popcorn films which deal with this (should this be set to spoiler?):

On Her Majesty's Secret Service
Superman: The Movie
Spiderman
Chinatown
Time Bandits
Walk of Fire / Ray / ... Walk Hard [?!?](unseen by me)

However... books I recommend:

Making Sense Out of Suffering (Peter Kreeft)
A Severe Mercy (soon to be a movie) - Sheldon Vanauken
A Grief Observed (CS Lewis) / A Grief Unveiled (Gregory Floyd)
Ragamuffin Gospel (Brennan Manning)

Thematically, "Last Tango in Paris" would qualify, but I can't see this film being of much practical help.

Some of these might be more appealing to "midwestern" men than others...and some have darker stories to tell.

About Schmidt
Ikiru
The Straight Story
Finding Nemo
Magnolia
Big Fish
Forrest Gump
Gladiator (for really Manly men, of course; anger can [and I would argue often should] be a large part of grief)
The Fisher King
Three Colors: Blue (some might think this is a particularly feminine story, but I do not)
Planes, Trains, and Automobiles (laughter is a great gift to the grieving)
Signs (a film I like much more than many here)
In America
Saving Private Ryan (could be HUGE if the parent was a veteran...)
also: good Jesus films; He was well acquainted with grief

As an aside, I'm not sure I'm a big fan of movies as therapy, especially for mourning, since it's so different for every individual. But if a film can help people understand life in a larger sense, and maybe make some connections to their own emotions, perhaps a film could be helpful as art, but not as therapy per se.

Grief can be so unpredictable. It's entirely possible that a single moment of an otherwise irrelevant (or even poorly made) film could hit a nerve and help get the healing started. Saving Private Ryan might be life-changing for the child of a WW2 veteran, but irrelevant for many others. The last thing someone in grief needs to be told is "you should feel like this." Whatever form this list takes, it should emphasize that it's just a starting place and might not be helpful for some.

Big Fish

The Accidental Tourist

AIRPLANE.

They could probably use a good laugh.

Marilyn Hotchkiss Ballroom Dancing and Charm School. Seriously.

Nobody mention Sleepless in Seattle yet? Not that I'd recommend it particularly...

Matt