Movies like Diary of a Tired Black Man (2009)
The best movies like Diary of a Tired Black Man (2009) are You Will Meet a Tall Dark Stranger (2010), Edges of the Lord (2001) and The Baltimorons (2025). If Diary of a Tired Black Man hooked you with its comedy and drama, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedC.R.A.Z.Y. (2005)7.5/10 from 535 votes
- NewestThe Baltimorons (2025)Released 2025
You Will Meet a Tall Dark Stranger (2010)
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 from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisEdges of the Lord (2001)
A 12-year-old Jewish boy hides with a family of Catholic peasant farmers to escape the Nazis.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisThe Baltimorons (2025)
A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisEnemies, a Love Story (1989)
A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisDelirious (2007)
Les, a small-time celebrity photographer desperate to make it big, befriends Toby, a homeless young man with no direction except a vague desire to become an actor. When by chance, Toby becomes romantically involved with K'Harma Leeds, the hottest pop star of the moment, Les grows jealous and plots revenge.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisNumb (2007)
Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink, but nothing works. The Golf Channel, lesbian exercise classes and a dizzying variety of pills get him through the day, but don't quite solve his problem. His writing partner tries everything to get him back to normal, but it's not until Hudson meets Sara that he finds a real motivation to get better and to actually start feeling again. From the writer of Deuce Bigalow, comes NUMB, a romantic comedy following an unusual man looking for strange love.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisCyrus (2010)
With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before long, the two are locked in a battle of wits for the woman they both love-and it appears only one man can be left standing when it's over.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisBreaking & Exiting (2018)
Harry, a charming house thief, gets more than he bargains for during an attempted burglary when he stumbles upon Daisy and decides to save her from herself, sending both of them into a darkly comedic journey of self discovery and love.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisPeace, Love & Misunderstanding (2011)
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.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisChéri (2009)
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.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisSidewalks of New York (2001)
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, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisJack Goes Boating (2010)
A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered on two working-class New York City couples.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisHe Said, She Said (1991)
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 alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisI Met a Girl (2020)
An aspiring musician struggling with schizophrenia falls for a mysterious woman who may be all in his head. When she suddenly vanishes, he takes off on a cross-country journey across Australia to find her, forcing his long-suffering brother to chase after him.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisLove Accidentally (2022)
Alexa and Jason are competing for a position at an advertising firm when their partners break up with them. Alexa mistakenly texts Jason, and they start a phone-only relationship. When they meet and the truth comes out, will true love prevail?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisDanny Deckchair (2003)
An unappreciated laborer's patience reaches breaking point when his girlfriend cancels a romantic holiday. Making light of the situation, he decides to tie hundreds of helium balloons to a chair in an outlandish bid to float to a new life.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisCherry (2010)
Ivy League Freshman, Aaron Milton (17) gets a different kind of education when he falls for Linda (34) a vivacious former wild-child who has returned to college to straighten out her life. The curriculum gets more challenging when Aaron meets Linda's sarcastic 14 year-old daughter, Beth - who quickly develops a crush on him. The math doesn't work in either direction but the dysfunctional triangle becomes a learning experience for all involved.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisHow to Please a Woman (2022)
When her all-male house-cleaning business gets out of control, a mature woman must embrace her own sexuality, if she is to make a new life for herself.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisStrictly Sexual (2008)
Two successful women, sick and tired of dating and relationships, decide to keep two young men in their pool house for strictly sexual purposes.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisRosaline (2022)
Left heartbroken after Romeo begins to pursue her cousin Juliet, Rosaline schemes to foil the famous romance and win back her guy in this comedic twist of Shakespeare's Romeo and Juliet.
Why it matches: Recommended by TMDB viewers · both romance & drama
Worth the HypeMovies like thisThe Wendell Baker Story (2005)
Luke Wilson plays a good-hearted ex-con who gets a job in a retirement hotel. Three elderly residents help him win back his girlfriend as he lends them a hand in fighting hotel corruption.
Why it matches: Similar story and style · both comedy & drama
SnoozefestMovies like thisLittle Voice (1998)
After the death of her father, Little Voice or LV becomes a virtual recluse, never going out and hardly ever saying a word. She just sits in her bedroom listening to her father's collection of old records of Shirley Bassey, Marilyn Monroe and various other famous female singers. But at night time, LV sings, imitating these great singers with surprising accuracy. One night she is overheard by one of her mother's boyfriends, who happens to be a talent agent. He manages to convince her that her talent is special and arranges for her to perform at the local night club, but several problems arise.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisC.R.A.Z.Y. (2005)
A young French Canadian, one of five boys in a conservative family in the 1960s and 1970s, struggles to reconcile his emerging identity with his father's values.
Why it matches: Similar story and style · both comedy & drama
Worth the HypeMovies like thisThe Bastards (2008)
A 24 hour period in the lives of Fausto and Jesus, two undocumented Mexican day-laborers in L.A. Each day another task, each day the same pressure to find money. They go about their daily routine, standing on the corner at the Home Improvement Store waiting for work to come. Today, the job they are given is well paid compared to their poor usual wages.
Why it matches: Similar story and style · both drama
Flame & Citron (2008)
Gunman Flame and his partner Citron assassinate Nazi collaborators for the Danish resistance. Assigned targets by their Allies-connected leader, Aksel Winther, they relish the opportunity to begin targeting the Nazis themselves. When they begin to doubt the validity of their assignments, their morally complicated task becomes even more labyrinthine.
Why it matches: Similar story and style · both drama
Popcorn FlickMovies like thisDelta (2008)
A man comes home to meet his mother and sister after many years away. He finds his mother living with a new boyfriend, and his sister to be grown-up. He begins to settle down in this new place by building a new home for himself on the delta. But when his sister moves in with him and the two begin a romance, there are tragic consequences.
Why it matches: Similar story and style · both drama
Dear Frankie (2004)
Nine-year-old Frankie and his single mum Lizzie have been on the move ever since Frankie can remember, most recently arriving in a seaside Scottish town. Wanting to protect her deaf son from the truth that they've run away from his father, Lizzie has invented a story that he is away at sea on the HMS Accra. Every few weeks, Lizzie writes Frankie a make-believe letter from his father, telling of his adventures in exotic lands. As Frankie tracks the ship's progress around the globe, he discovers that it is due to dock in his hometown. With the real HMS Accra arriving in only a fortnight, Lizzie must choose between telling Frankie the truth or finding the perfect stranger to play Frankie's father for just one day...
Why it matches: Similar story and style · both drama
Worth the HypeMovies like thisPalermo Shooting (2008)
After the wild lifestyle of a famous young German photographer almost gets him killed, he goes to Palermo, Sicily to take a break. Can the beautiful city and a beautiful local woman calm him down?
Why it matches: Similar story and style · both drama
Popcorn FlickMovies like thisLisbon Story (1994)
Wim Wenders' homage to Lisbon and films. A sound engineer obtains a mysterious postcard from a friend who at the moment is filming a film in Lisbon. He sets out across Europe to find him and help him.
Why it matches: Similar story and style · both drama
Worth the HypeMovies like thisAlistair1918 (2015)
A social work grad student’s film project on L.A. homelessness becomes something quite other when she and her friends encounter a man claiming to be from another time and place.
Why it matches: Similar story and style · both drama
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Frequently asked questions
What are the best movies like Diary of a Tired Black Man?
The closest matches to Diary of a Tired Black Man are You Will Meet a Tall Dark Stranger (2010), Edges of the Lord (2001) and The Baltimorons (2025). Below are 27 more, each with the reason it matches.
What should I watch after Diary of a Tired Black Man?
Start with You Will Meet a Tall Dark Stranger (2010), the closest match to Diary of a Tired Black Man.
What is the highest-rated movie like Diary of a Tired Black Man?
C.R.A.Z.Y. (2005), rated 7.5/10 by 535 TMDB users.
What is the newest movie like Diary of a Tired Black Man?
The Baltimorons (2025) is the most recent release on this list.
Are there English movies like Diary of a Tired Black Man?
Yes: You Will Meet a Tall Dark Stranger (2010), Edges of the Lord (2001) and The Baltimorons (2025).
How are movies similar to Diary of a Tired Black Man chosen?
First come films that Trakt’s viewers watch alongside Diary of a Tired Black Man, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.