Reviewed by: Cindy Hatcher
6 affordable festive musical films to see this holiday season
Reading time: 6 minutes
Sponsored

Looking for a unique way to celebrate the holiday season? This month, Sidewalk Film Center & Cinema is rolling out a lineup of charming musical films, from timeless classics like “The Wizard of Oz” to modern favorites like “La La Land.”
We spoke with the Sidewalk Film Center & Cinema team to learn more about the six movies in their Holiday Musical series.
1. The Wizard of Oz (1939)

“Wicked” fans, take note: This is where it all began on the big screen.
What to expect: When a tornado rips through Kansas, Dorothy (Judy Garland) and her dog, Toto, are whisked away in their house to the magical land of Oz. They follow the Yellow Brick Road toward the Emerald City to meet a few friends along the way.
Why you’ll love it:
“‘Growing up this classic film played in our house nonstop and introduced me to the magic and wonder of films. As America’s most famous fairy tale, The Wizard of Oz truly transports you into the world of its story.
Before Ariana and Cynthia, Judy Garland wowed us with her voice. Come see this film if you want to behold a technical marvel, experience a classic musical, and be swept over the rainbow. Make it a double feature with ‘The Wiz’ starring Diana Ross and Michael Jackson also playing at Sidewalk over the holidays!”
Jessica Chriesman, Director of Education + Outreach
- When:
- Friday, Dec. 12 | 2:15PM
- Saturday, Dec. 13 | 2:45PM
- Sunday, Dec. 14 | 12:30PM
- Thursday, Dec. 18 | 2:15PM
- Tickets: Available online
2. The Wiz (1978)
Looking for a different spin on The Wizard of Oz? See it from a different perspective in this retelling the debuted nearly 40 years later.
What to expect: When Harlem schoolteacher Dorothy (Diana Ross) tries to save her dog from a storm, she’s miraculously whisked away to an urban fantasy land called Oz. After accidentally killing the Wicked Witch of the East upon her arrival, Dorothy is told about the Wiz (Richard Pryor), a wizard who can help her get back to Manhattan. As Dorothy goes in search of the Wiz, she’s joined by the Scarecrow (Michael Jackson), the Tin Man (Nipsey Russell) and the Cowardly Lion (Ted Ross).
- When:
- Friday, Dec. 12 | 4:30PM
- Saturday, Dec. 13 | 5:00PM
- Sunday, Dec. 14 | 3:00PM
- Tickets: Available online
3. Singin’ in the Rain (1952)

Here’s one of the classics that pops to minds when you say “musical.” And for good reason: It’s pure joy and will have you dancing down 2nd Avenue back to your car.
What to expect: A silent film star falls for a chorus girl just as he and his delusionally-jealous screen partner are trying to make the difficult transition to talking pictures in 1920s Hollywood.
Why you’ll love it:
“I think ‘Singin’ in the Rain’ is the single best movie musical ever made.
No one has ever matched the invention and physicality of Gene Kelly, behind and in front of the camera. It’s vibrant, imaginative moviemaking with some of the most indelible musical sequences of all time, including Donald O’Connor’s “Make ‘Em Laugh” number, the “Broadway Melody” dream ballet sequence and the iconic performance of the title song.
If you haven’t seen it, there is no better way to check it off the watchlist than by seeing it on the big screen.”
Corey Craft, Cinema Programming Coordinator
- When:
- Saturday, Dec. 13 | 12:30PM + 7:45PM
- Thursday, Dec. 18 | 4:30PM
- Tickets: Available online
4. La La Land (2016)

Here’s a (relatively) more modern take on the classic musical that swept the Academy Awards in 2017.
What to expect: Mia (Emma Stone), an aspiring actress, serves lattes to movie stars in between auditions, and Sebastian (Ryan Gosling), a jazz musician, scrapes by playing cocktail party gigs in dingy bars, but as success mounts they are faced with decisions that begin to fray the fragile fabric of their love affair, and the dreams they worked so hard to maintain in each other threaten to rip them apart.
Why you’ll love it:
“With its painterly cinematography, rich color palette and references to golden-age musicals, the movie feels both timeless and modern, celebrating show business even as it acknowledges its heartbreaks. Its long takes, memorable songs, and dreamlike staging turn Los Angeles into a world where art becomes an expression of love, and for me, the entire experience was a warm, bittersweet joy from start to finish.”
Jennifer Freehling, Box Office Manager
- When:
- Friday, Dec. 19 | 2:15PM
- Saturday, Dec. 20 | 1:15PM + 6:30PM
- Sunday, Dec. 21 | 10:30AM
- Tuesday, Dec. 23 | 2:00PM
- Tickets: Available online
5. Chicago (2002)

See this film version of the longest-running Broadway play in history. You may pick up on a few themes from current times while you’re at it.
What to expect: Nightclub sensation Velma (Catherine Zeta-Jones) murders her philandering husband, and Chicago’s slickest lawyer, Billy Flynn (Richard Gere), is set to defend her. But when Roxie (Renée Zellweger) also winds up in prison, Billy takes on her case as well, turning her into a media circus of headlines. Neither woman will be outdone in their fight against each other and the public for fame and celebrity.
Why you’ll love it:
“One of the more recent examples of a great movie musical that echoes the Old Hollywood tradition so well. It may not be quite as family-friendly as the other selections, but it’s always just as fun.”
Nick Adrian, Marketing Manager
- When:
- Friday, Dec. 19 | 5:00PM
- Saturday, Dec. 20 | 4:00PM + 9:15PM
- Sunday, Dec. 21 | 3:30PM
- Monday, Dec. 22 | 2:00PM
- Tuesday, Dec. 23 | 7:30PM
- Tickets: Available online
6. Dreamgirls (2006)

Lovers of classic Motown and Muscle Shoals groups will feel right at home. See it now before it gets a revival run on Broadway next year.
What to expect: Deena (Beyoncé Knowles), Effie (Jennifer Hudson) and Lorrell (Anika Noni Rose) form a music trio called the Dreamettes. When ambitious manager Curtis Taylor Jr. (Jamie Foxx) spots the act at a talent show, he offers the chance of a lifetime, to be backup singers for a national star (Eddie Murphy). Taylor takes creative control of the group and eventually pushes the singers into the spotlight. However, one becomes the star, forcing another out, which teaches them about the high cost of fame.
Why you’ll love it:
“With a star-studded cast of Beyoncé, Jennifer Hudson, Jamie Foxx, Eddie Murphy (and much more) and a soundtrack for the ages, this is a musical that will have you on your feet right in the theater.”
Tripp Buckingham, Assistant Front of House Manager
- When:
- Friday, Dec. 19 | 7:30PM
- Saturday, Dec. 20 | 10:30AM
- Monday, Dec. 22 | 4:15PM
- Tuesday, Dec. 23 | 4:45PM
- Tickets: Available online
Planning to see one (or more!) of these films in Sidewalk’s Holiday Musical series? Tag us @bhamnow to let us know which ones you see!
Sponsored by:




10300 views