AI-Generated Collection
"Smashing the nation's worst crime ring!"
chicago, illinois; florida; witness; train; spats; sugar; dressing; valentine's day; cross dressing; st. valentine's day massacre
Some Like It Hot
1959-03-19
Comedy | Music | Romance | Crime
chicago, illinois, florida, witness, musician, mafia, cross dressing, train, band, spats, all girl band, st. valentine's day massacre, sugar, valentine's day, dressing
Inside The Mob's Bloody Valentine
2011-01-01
Documentary | Crime | History | TV Movie
prison, chicago, illinois, killing, fraud, interview, investigation, police, murder, jail, mafia, escape, gang, mobster, massacre, killer, death, al capone, st. valentine's day massacre, valentine's day, murder plot, unsolved, mob family, unsolved crime
The St. Valentine's Day Massacre
1967-06-30
History | Crime
chicago, illinois, prohibition era, historical figure, crime boss, shootout, gunfight, true crime, death, al capone, valentine's day, gun violence, 1920s
Chicago Syndicate
1955-07-01
Crime | Drama
chicago, illinois, gangster, noir
Valentine's Day
1959-10-26
Romance | Comedy
Crime Spree
2003-04-16
Comedy | Crime
chicago, illinois, fbi, gangster, hoodlum, american mafia
Some Like It Hot 2
Single Valentine
2013-02-07
Comedy | Romance
Be Mine
2017-02-14
Horror
valentine's day
The Whole Nine Yards
2000-02-18
Comedy | Crime
chicago, illinois, gangster, montreal, canada, mafia, dentist, hoodlum
WCW Clash of The Champions V: St. Valentine's Massacre
1989-02-15
champion, wrestling, massacre, st. valentine's day massacre, massacre survivor, clash
Hearts Are Thumps
1937-04-02
Comedy
our gang
Melody For Two
1937-05-01
Music | Romance
musical, big band
Twelfth Night
1955-11-21
Comedy | Romance | Drama
count, based on play or musical, mistaken identity, cross dressing
Chicago Confidential
1957-08-30
Action | Adventure | Crime | Drama
chicago, illinois, noir
Rogers Park
2017-10-19
Drama
chicago, illinois, secret, couple
Chi-Raq
2015-12-04
Drama | Crime | Comedy
chicago, illinois
Jake LaMotta vs. Sugar Ray Robinson VI
1951-02-14
Syncopation
1942-05-22
Music | Romance
chicago, illinois, jazz, world war i, louisiana, musician, music, playing piano, trumpet player
Valentine Days
2003-02-08
Comedy | Drama | Romance
Charleys Tante
1996-12-28
Comedy
aunt, cross dressing
Know Thy Wife
1918-12-30
Comedy
cross dressing
Valentin Valentin
2015-01-07
Crime
Girl Happy
1965-04-14
Comedy | Music | Romance
spring break, rock singer
Nickelodeon's Not So Valentine's Special
2017-02-12
Comedy
holiday, valentine's day
Valentine
2001-02-02
Horror | Thriller
mobbing, success, violence against women, revenge, serial killer, masked killer, slasher, valentine's day
Love at First Glance
2017-02-14
Drama | TV Movie
valentine's day
Mafia Girls
1969-01-01
Crime
Band of Girls Only
True Identity
1991-07-23
Comedy
new york city, hitman, mafia
Remo
2016-10-07
Comedy | Romance
cross dressing
2 in 1
2006-01-11
Comedy
cross dressing
Valentine Crush(ed)!
2009-02-15
Romance
bicycle accident, bicycle, falling in love, valentine's day, short
Frank
2014-05-02
Comedy | Drama | Mystery
identity, musician, music, friendship, mysterious, mental problems
My Secret Valentine
2018-02-03
Romance | TV Movie
valentine's day
The Girl from Chicago
1927-11-09
Action | Crime | Drama | Romance
Dinner For One
The Girl In the Barracks
1956-06-29
Comedy
army, cross dressing, conscripts, barracks, siblings
Guns Of Chicago
2012-08-13
Crime | Action | Comedy
gangster, cop, mafia, tragedy, shootout
Liberace: A Valentine Special
1979-09-03
Music | Comedy
1970s, music special
R.E.M. - Live
2008-01-01
Music
band
Vitalium, Valentine !
2017-07-14
Comedy
Valentine
2003-01-01
Comedy | TV Movie
Valentin DobrotivĂ˝
1942-07-31
Comedy
Kat and the Band
2020-01-13
Comedy
Shitcago
2015-11-11
Comedy
chicago, illinois
Juwanna Mann
2002-06-21
Comedy
sports, basketball, cross dressing, disguise, basketball player, man dressed as woman
Valentine's Break Up
2008-12-24
Comedy
short
Chicago
2002-12-26
Comedy | Crime | Drama
chicago, illinois, musical, jail, based on play or musical, lawyer, prison matron, jazz age, 1920s
Love and the City 2
2010-02-25
Comedy | Romance
Saint Valentine's Night
2016-03-10
Romance | Comedy
First a Girl
1935-11-07
Comedy
musical, cross dressing
Raw Deal
1986-06-06
Action | Crime | Thriller
chicago, illinois, undercover, fbi, gangster, mafia boss, bomb attack, 1980s
The Farewell Girls
2017-06-30
Drama | Comedy
music band
Laundry Day
Comedy | Music
Cheap Trick: Live at Chicagofest
1981-08-05
Music
chicago, illinois, concert, rock band, power pop, cheap trick
Christ(Off)
2018-07-11
Comedy
Charley's Aunt
1956-01-19
Comedy
aunt, cross dressing
Streetwalkin’ Cowboy
Crime
A Bird in the Bush
2008-06-25
Cathy's Valentine
1989-02-10
Animation | Comedy | Romance
based on comic, female protagonist, valentine's day, tv special
All Things Valentine
2016-01-31
Romance | Comedy | TV Movie
romantic comedy, valentine's day
Detroit Mob Confidential
2009-09-30
Documentary | Crime
chicago, illinois, organized crime, mafia, mob
The Boys from County Clare
2003-09-12
Romance | Comedy | Music
musician, music, ireland
Valentine & Cie
2007-01-01
Comedy | TV Movie | Romance
Doubles
2016-03-17
Comedy
mistaken identity, mafia
Dirty Deeds
2002-07-18
Crime | Comedy | Drama | Thriller
Rocker
2006-05-22
Drama | Comedy | Music
scandal, musician, rock group, rock band, music manager, struggling musician
Before Valentine
2009-02-05
Romance
A New Day... All Access
2007-12-07
Music | Documentary
Why Did Dragan Gather His Band
2017-05-11
Documentary | Music
Josie and the Pussycats
2001-04-06
Comedy | Music
manager, pop, secret, small town, garage, pop star, musician, female friendship, mtv, music, friendship, industry, celebrity, satire, conspiracy, subliminal , rock band, all girl band, culture, message, woman director, fortune, record deal, popular, pawns, music industry, subliminal message
Hospital Massacre
1981-10-16
Horror | Thriller
nurse, murder, stalking, serial killer, hospital, valentine's day
It Happened One Valentine's
2017-02-07
Romance | Comedy | TV Movie
pop star, valentine's day, lying
Some Like It Hot
1939-05-19
Comedy | Music | Romance
musical, boardwalk, singer, ring
Sugar Blues
2014-01-24
Chicago Cab
1997-01-01
Comedy | Drama
taxi, chicago, illinois, taxi driver, cab driver, day in a life