Most Similar Movies to Diamonds (1999)
If you are looking for movies like Diamonds (1999), you might like movies tagged with keyword : old man, son, teen boy, woman, heartwarming, amusing, canada, nevada, house, road, restaurant, casino, grief, hidden treasure, boxing, road trip, father/son relationship, adventure, quest, love, transformation, 1990s .
Cheaper by the Dozen 2 (2005), Loose Cannons (2010), Pieces of April (2003), A Christmas Tale (2008), This Is Where I Leave You (2014), Die Mommie Die! (2003), Vacation (2015) ... Let's take a look at the following list...

Cheaper by the Dozen 2 (2005)
The Bakers, while on vacation, find themselves competing with a rival family of eight children.
Stream Full Movie
Loose Cannons (2010)
The youngest son (Riccardo Scamarcio) of an Italian pasta magnate plans to announce he's gay so that he won't have to take over the family business -- but his brother (Alessandro Preziosi) makes a startling announcement of his own.
Stream Full Movie
Pieces of April (2003)
A wayward daughter invites her dying mother and the rest of her estranged family to her apartment for Thanksgiving dinner.
Stream Full Movie
A Christmas Tale (2008)
The troubled Vuillard family is no stranger to illness, grief, and banishment, but when their matriarch requires a bone-marrow transplant, the estranged clan reunites just in time for Christmas.
Stream Full Movie
This Is Where I Leave You (2014)
When their father passes away, four grown siblings are forced to return to their childhood home and live under the same roof together for a week, along with their over-sharing mother and an assortment of spouses, exes and might-have-beens.
Stream Full Movie
Die Mommie Die! (2003)
Trapped in a loveless marriage, an aging celebrity (Charles Busch) has an affair and plots to kill her husband.
Stream Full Movie
Vacation (2015)
Rusty Griswold takes his own family on a road trip to "Walley World" in order to spice things up with his wife and reconnect with his sons.
Stream Full Movie
Nebraska (2013)
An aging, booze-addled father makes the trip from Montana to Nebraska with his estranged son in order to claim a million-dollar Mega Sweepstakes Marketing prize.
Stream Full Movie
Blended (2014)
After a bad blind date, a man and woman find themselves stuck together at a resort for families, where their attraction grows as their respective kids benefit from the burgeoning relationship.
Stream Full Movie
Red Doors (2005)
The Wongs struggle to cope with life, love, and family dysfunction in the suburbs of New York.
Stream Full Movie
Life During Wartime (2009)
Friends, family, and lovers struggle to find love, forgiveness, and meaning in an almost war-torn world riddled with comedy and pathos.
Stream Full Movie
I Ought to Be in Pictures (1982)
Grandmother has nothing to say when Libby tells her that she is off to LA to look up Dad, a Hollywood screenwriter. Grandmother has been in a New York cemetery for six years and Dad has been out of Libby's life for 16 of her 19 years. Libby arrives in LA on a Tuesday and phones Dad the one night that Stephanie, who does Jane Fonda's hair, stays over. Stephanie is ther...Read all
Stream Full Movie
National Lampoon's European Vacation (1985)
The Griswolds win a vacation tour across Europe where the usual havoc ensues.
Stream Full Movie
The Kid (2000)
An unhappy and disliked image consultant gets a second shot at life when he is mysteriously confronted by an eight-year-old version of himself.
Stream Full Movie
Parental Guidance (2012)
Artie and Diane agree to look after their three grandkids when their type-A helicopter parents need to leave town for work. Problems arise when the kids' 21st-century behavior collides with Artie and Diane's old-school methods.
Stream Full Movie
Passed Away (1992)
A bunch of eccentric relatives gather for their patriarch's funeral.
Stream Full Movie
The Big Wedding (2013)
A long-divorced couple fakes being married as their family unites for a wedding.
Stream Full Movie
Last Summer in the Hamptons (1995)
This moving story was the swan song of actress Viveca Lindfors, who died unexpectedly soon after completing it. It's a fitting tribute, as the film explores the last performance in the ancestral home of a large family of actors.
Stream Full Movie