99		Follow the Fleet (Comedy, Musical, Romance, 1936)
96		Shall We Dance (Comedy, Musical, Romance, 1937)
93		Flying Down to Rio (Comedy, Musical, Romance, 1933)
87		Cover Girl (Comedy, Musical, Romance, 1944)
85		Let's Make Love (Comedy, Musical, Romance, 1960)
84		In the Navy (Comedy, Musical, Romance, 1941)
84		You'll Never Get Rich (Comedy, Musical, Romance, 1941)
81		Hands Across the Table (Comedy, Romance, 1935)
75		Gigi (Comedy, Musical, Romance, 1958)
70		Royal Wedding (Comedy, Musical, Romance, 1951)
70		Spinout (Comedy, Musical, Romance, 1966)
69		State Fair (Musical, Romance, 1945)
69		Roberta (Comedy, Musical, Romance, 1935)
68		You Were Never Lovelier (Comedy, Musical, Romance, 1942)
68		Dancing Lady (Musical, Comedy, Romance, 1933)
67		Cyrus (Comedy, Drama, Romance, 2010)
67		Now You Know (Comedy, Romance, 2002)
67		Topper (Comedy, Fantasy, Romance, 1937)
67		The Puffy Chair (Comedy, Drama, Romance, 2005)
67		Summer Stock (Musical, Romance, 1950)
67		Brigadoon (Fantasy, Musical, Romance, 1954)
66		Love Crazy (Comedy, Romance, 1941)
65		Top Hat (Comedy, Musical, Romance, 1935)
65		Silk Stockings (Comedy, Musical, Romance, 1957)
65		Gentlemen Prefer Blondes (Comedy, Crime, Musical, Romance, 1953)
64		The Gay Divorcee (Comedy, Musical, Romance, 1934)
62		Once Upon a Time in the Midlands (Comedy, Drama, Romance, 2002)
62		Oklahoma! (Musical, Romance, Western, 1955)
62		Vivacious Lady (Comedy, Romance, 1938)
62		Pillow Talk (Comedy, Romance, 1959)
62		Kiss Me, Stupid (Comedy, Romance, 1964)
62		The Wedding Singer (Comedy, Music, Romance, 1998)
62		A Month by the Lake (Comedy, Drama, Romance, 1995)
61		Curly Top (Family, Musical, Romance, 1935)
60		Romance on the High Seas (Comedy, Musical, Romance, 1948)
60		Sweet Charity (Comedy, Drama, Music, Romance, 1969)
59		Babes on Broadway (Comedy, Musical, Romance, 1941)
58		Ninotchka (Comedy, Romance, 1939)
58		The Merry Widow (Musical, Comedy, Romance, 1934)
58		Bringing Up Baby (Comedy, Family, Romance, 1938)
57		Love and Other Catastrophes (Comedy, Romance, 1996)
57		Baby Mama (Comedy, Romance, 2008)
57		It's in the Water (Comedy, Romance, 1997)
57		Music and Lyrics (Comedy, Music, Romance, 2007)
57		Blind Dating (Comedy, Romance, 2006)
57		Friends with Kids (Comedy, Drama, Romance, 2011)
57		Zus & zo (Comedy, Fantasy, Romance, 2001)
57		Happy, Texas (Comedy, Crime, Romance, 1999)
57		New York Stories (Comedy, Drama, Romance, 1989)
56		Wife vs. Secretary (Comedy, Drama, Romance, 1936)
55		Paint Your Wagon (Comedy, Drama, Musical, Romance, 1969)
55		Star! (Biography, Comedy, Drama, Romance, 1968)
55		Darling Lili (Comedy, Drama, Musical, Romance, 1970)
55		Swing Time (Comedy, Musical, Romance, 1936)
55		The Unsinkable Molly Brown (Biography, Comedy, Musical, Romance, 1964)
55		Happy Feet (Animation, Comedy, Family, Romance, 2006)
55		Unconditional Love (Comedy, Drama, Musical, Romance, 2002)
55		A Damsel in Distress (Comedy, Musical, Romance, 1937)
54		Holiday Inn (Comedy, Drama, Musical, Romance, 1942)
53		The Gang's All Here (Comedy, Musical, Romance, 1943)
53		Meet Me in St. Louis (Comedy, Drama, Family, Romance, 1944)
52		Ball of Fire (Comedy, Romance, 1941)
52		Going Hollywood (Musical, Romance, 1933)
52		Charlie Bartlett (Comedy, Drama, Romance, 2007)
52		Only You (Comedy, Romance, 1994)
52		What Happens in Vegas (Comedy, Romance, 2008)
52		Forgetting Sarah Marshall (Comedy, Drama, Romance, 2008)
52		Back to School (Comedy, Romance, Sport, 1986)
52		What Women Want (Comedy, Fantasy, Romance, 2000)
52		South Pacific (Musical, Romance, War, 1958)
52		Ruggles of Red Gap (Comedy, Romance, 1935)
52		Barefoot in the Park (Comedy, Romance, 1967)
52		Tadpole (Comedy, Drama, Romance, 2000)
51		The Band Wagon (Comedy, Musical, Romance, 1953)
51		Victor Victoria (Comedy, Music, Musical, Romance, 1982)
50		The Pajama Game (Comedy, Drama, Musical, Romance, 1957)
50		Mamma Mia! (Comedy, Family, Musical, Romance, 2008)
50		Funny Face (Comedy, Musical, Romance, 1957)
50		Jhankaar Beats (Comedy, Musical, Romance, 2003)
50		They Live by Night (Crime, Film-Noir, Romance, 1948)
50		Funny Girl (Biography, Comedy, Drama, Romance, 1968)
50		Show Boat (Comedy, Drama, Musical, Romance, 1936)
49		The Cameraman (Comedy, Romance, Family, 1928)
49		It Happened on Fifth Avenue (Comedy, Music, Romance, 1947)
48		Adam's Rib (Comedy, Drama, Romance, 1949)
48		Lonesome (Comedy, Drama, Romance, 1928)
48		Breakfast at Tiffany's (Comedy, Drama, Romance, 1961)
47		Before We Go (Comedy, Drama, Romance, 2014)
47		Living Out Loud (Comedy, Drama, Romance, 1998)
47		Happythankyoumoreplease (Comedy, Drama, Romance, 2010)
47		Mambo Italiano (Comedy, Drama, Romance, 2003)
47		Kate & Leopold (Comedy, Fantasy, Romance, 2001)
47		Dream Wife (Comedy, Romance, 1953)
47		The Rebound (Comedy, Romance, 2009)
47		A Lot Like Love (Comedy, Drama, Romance, 2005)
47		Paper Heart (Comedy, Drama, Romance, 2009)
47		Love Affair (Comedy, Drama, Romance, 1939)
46		One Way Passage (Comedy, Drama, Romance, 1932)
46		I Love You Again (Comedy, Romance, 1940)
46		Sun Valley Serenade (Comedy, Music, Romance, 1941)
46		Twentieth Century (Comedy, Romance, 1934)
45		The Thing Called Love (Comedy, Drama, Music, Romance, 1993)
45		Kismet (Adventure, Musical, Fantasy, Romance, 1955)
45		Tortilla Flat (Comedy, Drama, Romance, 1942)
45		Show Boat (Drama, Family, Musical, Romance, 1951)
45		The Tales of Hoffmann (Fantasy, Music, Musical, Romance, 1951)
45		Elf (Comedy, Family, Fantasy, Romance, 2003)
45		Another Thin Man (Comedy, Crime, Drama, Romance, 1939)
45		Florence Foster Jenkins (Biography, Comedy, Drama, Romance, 2016)
45		Cain and Mabel (Comedy, Musical, Romance, 1936)
44		The Apartment (Comedy, Drama, Romance, 1960)
44		The Naughty Nineties (Comedy, Crime, Romance, 1945)
44		Annie Hall (Comedy, Romance, 1977)
44		Footlight Parade (Comedy, Musical, Romance, 1933)
44		Road to Singapore (Comedy, Musical, Romance, 1940)
44		Pot o' Gold (Comedy, Musical, Romance, 1941)
44		42nd Street (Comedy, Musical, Romance, 1933)
43		Girl Crazy (Comedy, Musical, Romance, 1943)
43		Bachelor Mother (Comedy, Romance, 1939)
43		I'm No Angel (Comedy, Musical, Romance, 1933)
43		Stage Door Canteen (Comedy, Musical, Romance, 1943)
43		Love Me Tonight (Comedy, Musical, Romance, 1932)
43		Horse Feathers (Comedy, Musical, Romance, 1932)
43		The Awful Truth (Comedy, Romance, 1937)
43		The Smiling Lieutenant (Comedy, Romance, Musical, 1931)
43		Dames (Comedy, Musical, Romance, 1934)
42		Leap of Faith (Comedy, Drama, Romance, 1992)
42		The Boys & Girl from County Clare (Comedy, Music, Romance, 2003)
42		Hollywood Canteen (Comedy, Musical, Romance, 1944)
42		Teacher's Pet (Comedy, Romance, 1958)
42		That Awkward Moment (Comedy, Romance, 2014)
42		The Story of Vernon and Irene Castle (Biography, Musical, Romance, 1939)
42		New Year's Eve (Comedy, Romance, 2011)
42		His Girl Friday (Comedy, Drama, Romance, 1940)
42		Gun Shy (Comedy, Crime, Romance, 2000)
42		Valley Girl (Comedy, Romance, 1983)
42		Boca a boca (Comedy, Romance, 1995)
42		One Hour with You (Comedy, Musical, Romance, 1932)
42		Merrily We Live (Comedy, Romance, 1938)
42		Get Over It (Comedy, Romance, 2001)
42		Good News (Comedy, Musical, Romance, 1947)
42		About Adam (Comedy, Romance, 2000)
42		Life Partners (Comedy, Romance, 2014)
42		Singin' in the Rain (Comedy, Musical, Romance, 1952)
42		Soldier in the Rain (Comedy, Drama, Romance, 1963)
42		Man Up (Comedy, Drama, Romance, 2015)
42		Brève traversée (Comedy, Drama, Romance, 2001)
42		Two Family House (Comedy, Drama, Romance, 2000)
42		For Love or Money (Comedy, Drama, Romance, 1993)
42		New York, I Love You (Comedy, Drama, Romance, 2008)
41		White Christmas (Comedy, Musical, Romance, 1954)
41		The Devil Is a Woman (Comedy, Drama, Romance, 1935)
41		On the Town (Comedy, Musical, Romance, 1949)
41		The Major and the Minor (Comedy, Romance, 1942)
41		The Love Parade (Comedy, Musical, Romance, 1929)
41		The Music Man (Comedy, Musical, Romance, 1962)
41		The Boy Friend (Comedy, Musical, Romance, 1971)
40		Age of Consent (Biography, Comedy, Drama, Romance, 1969)
40		Tea for Two (Comedy, Musical, Romance, 1950)
40		Romance & Cigarettes (Comedy, Musical, Romance, 2005)
40		Frankie and Johnny (Comedy, Musical, Romance, 1966)
40		Thoroughly Modern Millie (Comedy, Musical, Romance, 1967)
40		Live a Little, Love a Little (Comedy, Musical, Romance, 1968)
40		Three Little Words (Biography, Comedy, Musical, Romance, 1950)
40		Take Me Out to the Ball Game (Comedy, Musical, Romance, 1949)
40		The Pirates of Penzance (Comedy, Musical, Romance, 1983)
40		In the Good Old Summertime (Comedy, Musical, Romance, 1949)
40		Love's Labour's Lost (Romance, Comedy, Musical, 2000)
40		The Curse of the Jade Scorpion (Comedy, Crime, Mystery, Romance, 2001)
40		The Inspector General (Comedy, Musical, Romance, 1949)
40		Girl Happy (Comedy, Musical, Romance, 1965)
40		Kissin' Cousins (Comedy, Musical, Romance, 1964)
40		Guys and Dolls (Comedy, Musical, Romance, 1955)
40		Flower Drum Song (Comedy, Musical, Romance, 1961)
40		Bells Are Ringing (Comedy, Musical, Romance, 1960)
40		Artists and Models (Comedy, Musical, Romance, 1955)
40		Damn Yankees! (Comedy, Musical, Romance, 1958)
40		Music Within (Biography, Comedy, Drama, Romance, 2007)
40		My Sister Eileen (Musical, Comedy, Romance, 1955)
40		Follow That Dream (Comedy, Musical, Romance, 1962)
40		Earth Girls Are Easy (Comedy, Musical, Romance, 1988)
40		High Society (Comedy, Musical, Romance, 1956)
40		Beach Party (Comedy, Musical, Romance, 1963)
40		Calamity Jane (Comedy, Musical, Romance, 1953)
40		It Happened at the World's Fair (Comedy, Musical, Romance, 1963)
40		Kiss Me Kate (Comedy, Musical, Romance, 1953)
40		On Moonlight Bay (Comedy, Musical, Romance, 1951)
40		The Tender Trap (Comedy, Musical, Romance, 1955)
40		Tales of Manhattan (Comedy, Drama, Romance, 1942)
40		Anomalisa (Animation, Comedy, Drama, Romance, 2015)
40		To Have and Have Not (Adventure, Comedy, Romance, 1944)
40		Everyone Says I Love You (Comedy, Musical, Romance, 1996)
40		The Lizzie McGuire Movie (Adventure, Comedy, Family, Romance, 2003)
40		I'll Be There (Comedy, Musical, Romance, 2003)
40		Roxie Hart (Comedy, Crime, Romance, 1942)
40		The Emperor Waltz (Comedy, Musical, Romance, 1948)
39		Some Like It Hot (Comedy, Romance, 1959)
39		Groundhog Day (Comedy, Fantasy, Romance, 1993)
38		Wake Up Sid (Comedy, Drama, Romance, 2009)
38		Angel on My Shoulder (Comedy, Fantasy, Romance, 1946)
38		The Solid Gold Cadillac (Comedy, Romance, 1956)
38		Once Upon a Honeymoon (Adventure, Comedy, Drama, Romance, 1942)
38		Love with the Proper Stranger (Comedy, Drama, Romance, 1963)
38		The Broadway Melody (Musical, Romance, 1929)
38		Garden State (Comedy, Drama, Romance, 2004)

Notes: Movies similar to Carefree, Movies like Carefree, Comedy, Musical, Romance, Mark Sandrich, Fred Astaire, Ginger Rogers, Ralph Bellamy, Luella Gear, Films, Video, Movie Similarities