Movies Like Wilby Wonderful

If you liked Wilby Wonderful (2004), a comedy and drama movie directed by Daniel MacIvor, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Chéri (2009)
★ 6.1/10Also drama and comedy
The son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.
2
He Said, She Said (1991)
★ 5.9/10Also comedy and drama
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions…
3
You Will Meet a Tall Dark Stranger (2010)
★ 5.9/10Also comedy and drama
Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling…
4
Maudie (2016)
★ 7.8/10Also drama and romance
Canadian folk artist Maud Lewis falls in love with a fishmonger while working for him as a live-in housekeeper.
5
Sidewalks of New York (2001)
★ 6.1/10Also comedy and drama
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives…
6
Irreplaceable You (2018)
★ 7/10Also comedy and drama
A stunning cancer diagnosis spurs Abbie to seek a future girlfriend for fiancé and childhood sweetheart Sam, who's clueless when it comes to dating.
7
Is This Thing On? (2025)
★ 6.6/10Also comedy and drama
As their marriage quietly unravels, Alex faces middle age and an impending divorce, seeking new purpose in the New York comedy scene while Tess confronts the sacrifices she made for their family—forcing them to…
8
A California Christmas: City Lights (2021)
★ 6.6/10Also romance and comedy
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.
9
L.A. Without a Map (1999)
★ 5.8/10Also drama and comedy
An aspiring Hollywood actress, on a visit to a charming North England town, has a brief fling with the town undertaker, who also writes obituaries for the local paper. Returning home, where she works as a waitress at a…
10
Peace, Love & Misunderstanding (2011)
★ 5.8/10Also comedy and drama
A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce.
11
The Object of My Affection (1998)
★ 5.8/10Also drama and romance
A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.
12
Not Easily Broken (2009)
★ 6.3/10Also drama and romance
A car accident and shifting affections test the bond between a married couple.
13
Griffin & Phoenix (2006)
★ 7.1/10Also comedy and drama
A terminally ill man falls in love with a woman who has a secret that threatens their time spent together.
14
The Nanny Diaries (2007)
★ 6.4/10Also comedy and drama
A college graduate goes to work as a nanny for a rich New York family. Ensconced in their home, she has to juggle their dysfunction, a new romance, and the spoiled brat in her charge.
15
A California Christmas (2020)
★ 6.4/10Also comedy and romance
With his carefree lifestyle on the line, a wealthy charmer poses as a ranch hand to get a hardworking farmer to sell her family’s land before Christmas.
16
Elizabethtown (2005)
★ 6.2/10Also comedy and drama
Drew Baylor is fired after causing his shoe company to lose hundreds of millions of dollars. To make matters worse, he's also dumped by his girlfriend. On the verge of ending it all, Drew gets a new lease on life when…
17
The Baltimorons (2025)
★ 6.3/10Also comedy and drama
A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.
18
Father of the Bride (2022)
★ 6.3/10Also romance and comedy
A father comes to grips with his daughter’s upcoming wedding through the prism of multiple relationships within a big, sprawling Cuban-American family.
19
A Thousand Words (2012)
★ 6.1/10Also drama and comedy
Jack McCall is a fast-talking literary agent, who can close any deal, any time, any way. He has set his sights on New Age guru Dr. Sinja for his own selfish purposes. But Dr. Sinja is on to him, and Jack’s life comes…
20
Drive Me Crazy (1999)
★ 6.6/10Also romance and comedy
Nicole and Chase live next door to each other but are worlds apart. However, they plot a scheme to date each other in order to attract the interest and jealousy of their respective romantic prey. But in the mist of…