7 Classic Hollywood Films To Watch During The Holidays!

Nothing brings me holiday cheer quite like curling up on the sofa and watching an old, often black-and-white, film starring actors with perfectly polished transatlantic accents. There’s something about the glamour of Classical Hollywood Cinema that creates a distinctly festive feeling. From sharp-tongued screwball comedies to sweeping, heartfelt melodramas, I’ve compiled my favorite movies from this era to watch during Christmastime!

1. Bringing Up Baby (1938) 

This screwball comedy centers on a reserved paleontologist (Cary Grant) whose life is upended by the unpredictable Susan (Katharine Hepburn) and her pet leopard. The film’s rapid-fire dialogue and escalating absurdity make it the perfect choice for when you’re in the mood for pure laughter. Add to that Katharine Hepburn’s fabulous wardrobe, and the result is one of Hollywood’s most iconic films. (Stream on Tubi)

2. The Philadelphia Story (1940) 

High-society heiress Tracy Lord (Katharine Hepburn) finds her perfectly planned wedding disrupted by the sudden arrival of her ex-husband (Cary Grant) and an unexpected tabloid journalist (James Stewart). This delightful romantic comedy brings together three legendary Hollywood icons, making it a must-watch. (Stream on Tubi)

3. Charade (1963) 

This romantic thriller follows a wealthy woman (Audrey Hepburn) drawn into a web of mystery after her husband’s sudden death and a chance encounter with a charming stranger (Cary Grant). Suspenseful and witty, it’s a perfect balance of romance and intrigue, and, personally, it’s my favorite Audrey Hepburn film (and, famously, Blair Waldorf’s too). (Stream on Prime Video, Pluto TV, Tubi, and PLEX)

4. Stella Dallas (1937)

This tearjerker tells the story of a devoted mother (Barbara Stanwyck) who sacrifices everything to give her daughter (Anne Shirley) a better life. The film serves as a powerful reminder to appreciate our mothers and families, even if they’re occasionally driving us a little crazy during the holidays. (Stream on Prime Video, Pluto TV, and PLEX)

5. Holiday (1938)

Johnny (Cary Grant) is engaged to the youngest daughter of a wealthy, status-driven family, but unexpectedly falls for his fiancée’s free-spirited older sister, Linda (Katharine Hepburn). Set during the Christmas season, the film is a perfect holiday watch, capturing the importance of happiness and generosity. (Available on VOD/Digital)

6. Now, Voyager (1942)

This film follows Charlotte Vale (Bette Davis), a repressed and wealthy woman living under the strict control of her domineering mother. After receiving life-altering psychiatric care from Dr. Jaquith (Claude Rains), Charlotte reclaims her independence. On a cruise, she falls for Jerome (Paul Henreid), a married man, in a romance that’s bittersweet and heart-wrenching. (Available on VOD/Digital)

7. Imitation of Life (1934) 

The film follows two single mothers, one Black (Louise Beavers) and one white (Claudette Colbert), who begin a successful business together and form a friendship amid deep emotional struggles and racial tensions. Like Stella Dallas, it will make you appreciate family. Plus, its impact was so strong that Time Magazine named it one of the 25 Most Important Films About Race. (Available on VOD/Digital)