Most Similar Movies to Neil Simon's The Odd Couple II (1998)
If you are looking for movies like Neil Simon's The Odd Couple II (1998), you might like movies tagged with keyword : comedy, sequel, bromance, road movie, humor, midlife crisis, personality clash, classic adaptation, marital issues, nostalgia, slapstick, cultural differences, los angeles, new york, travel, conflict, gags, iconic characters, 1990s, life chaos .
National Lampoon's Vacation (1983), National Lampoon's European Vacation (1985), Laurel and Hardy's Laughing '20s (1965), The Sunshine Boys (1975), The Trip to Italy (2014), Last Vegas (2013), Home for the Holidays (1995) ... Let's take a look at the following list...

National Lampoon's Vacation (1983)
The Griswold family's cross-country drive to the Walley World theme park proves to be much more arduous than they ever anticipated.
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National Lampoon's European Vacation (1985)
The Griswolds win a vacation tour across Europe where the usual havoc ensues.
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Laurel and Hardy's Laughing '20s (1965)
This anthology, compiled by Robert Youngson, presents a series of silent short films from the 1920s starring the celebrated comedy duo of Stan Laurel and Oliver Hardy. In these early collaborations, Hardy plays an uncle embarrassed by the kilt of his Scottish nephew (Stan Laurel), and later the duo portrays a pair of inept butlers at a socialite's lavish dinner. The collection also features films by lesser-known silent comedians including Charley Chase and Max Davidson.
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The Sunshine Boys (1975)
After a long separation, two former vaudeville partners reunite to renew their friendship and their feud.
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The Trip to Italy (2014)
Two men, six meals in six different places on a road trip around Italy. Liguria, Tuscany, Rome, Amalfi and ending in Capri.
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Last Vegas (2013)
Four friends take a break from their day-to-day lives to throw a bachelor party in Las Vegas for their last remaining single pal.
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Home for the Holidays (1995)
After losing her job, making out with her soon-to-be former boss, and finding out that her daughter plans to spend Thanksgiving with her boyfriend, Claudia Larson faces spending the holiday with her family.
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The Groomsmen (2006)
A groom (Ed Burns) and his four attendants wrestle with issues related to friendship and maturity a week before the big day.
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Blind Date (1987)
A workaholic needs a date for a dinner with new important clientele, but who his brother sets him up with could lead to disaster.
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Sgt. Bilko (1996)
Sgt. Bilko is a well-liked conman in charge of the army base's motor pool, developing a hover tank and unofficially of gambling etc. One man hates Bilko and he's coming to inspect the base for possible closure.
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Klown Forever (2015)
Looking to save their strained relationship, a man (Frank Hvam) follows his best friend (Casper Christensen) to Hollywood.
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Dumb and Dumber To (2014)
20 years since their first adventure, Lloyd and Harry go on a road trip to find Harry's newly discovered daughter, who was given up for adoption.
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The Climb (2019)
Two lifelong pals test the boundaries of their friendship when a woman comes between them.
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The Sin of Harold Diddlebock (1947)
After being fired from his office job, Harold Diddlebock (Harold Lloyd) gets drunk, goes on a wild binge, and buys a near-bankrupt circus.
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City Slickers II: The Legend of Curly's Gold (1994)
One year after their first western adventure, Mitch Robbins and his friends discover a treasure map that belonged to their late trail guide Curly and they set out to discover its secrets.
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It's Always Fair Weather (1955)
A talk-show staffer (Cyd Charisse) puts a fight manager (Gene Kelly), adman (Dan Dailey) and cook on TV 10 years after they parted as GIs.
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Scooby-Doo on Zombie Island (1998)
Scooby (Scott Innes) and the rest of the Mystery, Inc., crew encounter creepy characters at a haunted house on a Louisiana bayou.
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Grown Ups 2 (2013)
After moving his family back to his hometown to be with his friends and their kids, Lenny finds out that between old bullies, new bullies, schizo bus drivers, drunk cops on skis, and four hundred costumed party crashers sometimes crazy follows you.
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