Anna Chlumsky
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Anna Chlumsky is one lady who has been in the public eye for the most parts of her life. She is an actress who featured in her very first movie (a comedy-drama film titled My Girl in 1991) when she was just a kid. Though the movie wasn’t a major box office hit, it was its 1994 sequel that made her not only famous but also a bonafide child star. Furthermore, My Girl 2 saw her win the Young Artist Award for Best Performance by a Young Actress Starring in a Motion Picture in 1995. Afterward, Anna Chlumsky’s filmography has grown to boast of a good number of films and TV shows which have also won her a couple of awards.

As an adult, she has been able to share her acting chops with the world on various film projects (both in movies and on television shows). Some of her most acclaimed performances can be witnessed in projects such as Veep (2012 – 2019), Miracle in the Woods (1997),  Gold Diggers: The Secret of Bear Mountain (1995) amongst others. In as much as Anna has made a good number of great movies, there are still some movies of hers that aren’t so great. Therefore, in consideration of various rankings, critic reviews and box office numbers here is a list of Anna Chlumsky films and TV shows rated from the best to the worst.

Anna Chlumsky’s Filmography Ranked From Best to Worst

1. Veep (2012 – 2019)

Anna Chlumsky
Anna Chlumsky and cast on an episode of Veep

On the top of our list of Anna Chlumsky filmography, the HBO television comedy series, Veep, takes the crown. The series which became available for viewing between April 22, 2012, to May 12, 2019, happens to be a political satire that was created by Armando Iannucci. It follows the life of the character Selina Meyer (played by Julia Louis-Dreyfus), a fictional vice president who works with her team passionately in order to leave a remarkable legacy in the political scene. 

So far, Anna’s performance as Amy Brookheimer (a political staffer who served as Vice President’s chief of staff, under both Vice President Selina Meyer and Jonah Ryan) in Veep has been one of the most lauded works of hers and this has been further reinforced by the nominations and awards won. Anna Chlumsky earned six Primetime Emmy Award nominations for Outstanding Supporting Actress in a Comedy Series for Veep in(2012). In 2015, she earned herself a ‘Gold Derby Awards’ for Comedy Supporting Actress for the same series.

2. My Girl (1991)

Anna Chlumsky
Anna Chlumsky and Macualay Culkin in My Girl

The second entry on our list for Anna Chlumsky filmography is the movie My Girl released in 1991. This movie happens to be the feature film debut project that made Anna Chlumsky a child star. In the film, she played the role of Vada Sultenfuss an 11-year-old girl whose mother died two days after giving birth to her. Her character is hyperactive and one where her father doesn’t understand her much. What makes the movie most endearing to fans is the love angle thrown in by the writer of the movie, Laurice Elehwany.

Anna’s young love interest was played by the charming Macaulay Culkin, who gained fame by his top-notch performance in the movie series, Home Alone. The film earned Anna and Macaulay Best On-Screen Duo and won Best Kiss at the MTV Movie Awards. Other notable casts featured in the movie include Jamie Lee Curtis, Dan Aykroyd among others. 

3. My Girl 2 (1994)

Anna Chlumsky
Anna Chlumsky and Austin O’Brien
The comedy-drama film, My Girl 2, was released in the year 1994. It serves as a sequel to My Girl, which was first released in the year 1991. In this movie, Anna played the role of 13 year old “Vada Sultenfuss” a budding teen who was given a holiday assignment to write about someone she admires but has never met. She chose to write about her late mother who died few days after giving birth to her. This assignment made her convince her father to let her travel to Los Angeles to stay with her uncle so she could learn more about her late mother.
What made this movie win critics and fans over is the storyline which admittedly wasn’t a totally new idea, however, it’s ability to connect with the audience on an emotional level was it’s winning factor. In the movie, Austin O’Brien played the role of Nick, who is the son of Vada’s uncle(Phil played by Richard Masur) and his girlfriend. Though Nick started off as sulky towards Vada, he soon warmed up to her and even joined in the quest to help Vada find out more about her late mother. Other featured casts in the movie include; Roland Thomson, Dan Aykroyd, Christine Ebersole, Jamie Lee Curtis e.t.c.

4. Miracle in the Woods (1997)

Anna Chlumsky
Anna Chlumsky and Dela Reese

Anna Chlumsky’s career as an actress has seen her feature in a good number of inspirational and heartwarming movies, Miracle in the Woods is one of such movies. This film tells the story of two sisters, Sarah (Meredith Baxter) and Wanda (Patricia Heaton), who are at loggerheads with each other. When their mother died, she left them a home as an inheritance.

While Sarah wants the house sold because of the financial issues she has, Wanda on the other hands insists that the property be preserved. The whole squabble would lead them to discover that the house has been occupied by a strange old lady named Lilly Cooper (Della Reese). Anna, on the other hand, plays the role of Sarah’s curious teenage daughter (Gina). The movie was directed by Arthur Allan Seidelman. 

5. Gold Diggers: The Secret of Bear Mountain (1995)

Anna Chlumsky filmography
Gold Diggers: The Secret of Bear Mountain (1995)

Fifth on our ranking of Anna Chlumsky’s filmography from best to worst is Gold Diggers, a film where Anna played the role of a teenager (Jody) who is a tomboy. She is seen as a misfit in her small town and has a series of problems with her mum and her mother’s boyfriend as well. Soon, a new girl her age named Beth Easton (played by Christina Ricci) moves into the small town and the pair quickly became friends. The Beth later had a dream where she is supposed to go in search of lost gold left hidden by Molly Morgan, a legendary woman in Bear Mountain. She tells Jody about it and the pair decided to go on the quest together.

6. Uncle Buck(1989)

Anna Clumsky in a scence of Uncle Buck

Uncle Buck is an American comedy film which easily gained the acceptance of fans and critics alike because it featured Anna Chlumsky and Macaulay Culkin yet again. Though Anna’s role was a small one, the overall tone of the movie was well-received. The story tells of an Uncle who became the last option his brother had of a baby sitter. The character, Buck (John Candy) is quite huge and cheesy sometimes and though his little relatives didn’t like him at first, they soon grow quite fond of him.

7. A Child’s Wish (1997)

Anna Chlumsky and co-star
This American made-for-television movie was released in the year 1997. Based on true-life events, the story sees Anna Chlumsky play the role of a critically ill 16-year-old girl named Missy who was battling cancer. Her father, Ed Chandler (played by John Ritter) was fired from his job because he took time off to cater to his sick daughter. As a result of this Ed Chandler rather than accept the termination decided to fight back by soliciting help from a United States senator. Fortunately, this led to the passage of the Family and Medical Leave Act. The movie was directed by Waris Hussein and star other actors including; Sarah Chalke, Tess Harper, Karl David-Djerf e.t.c.

8. The Good Guy (2010)

Anna Chlumsky filmography
Anna Chlumsky and Co-star Alexis Bledel in The Good Guy

Released in 2010, this romantic comedy movie is about a man named Tommy (played by Scott Porter) who has a great job in finance and a beautiful girlfriend named Beth (played by Alexis Bledel). In the firm he works at, he had to recommend someone new to take the place of a key employee who left the firm. This new employee named Daniel(played by (Bryan Greenberg) came into his new job as one who though attractive was quite tensed around ladies.

This prompted Tommy to tutor him on how to dress and get the ladies. Soon Daniel gets better at his overall outlook and even join a book club. Unfortunately for Tommy, it happens to be the same book club his girlfriend Beth is a part of and both Daniel and Beth become quite close. This, in turn, made Tommy quite uneasy as he ponders if his tutelage of Daniel has made him attractive to his girlfriend. The movie was written and directed by Julio DePietro and had Anna Chlumsky play the role of Lisa.

9. 12 Men of Christmas(2009)

Anna Chlumsky with Jefferson Brown

In this film, Anna Chlumsky played the role of Jan Lucas. Stars such as Kristin Chenoweth, Stephen Huszar, Josh Hopkins, Erin Dilly and more were cast to interpret the story of a lady, E.J. Baxter (played by Kristin Chenoweth), who has a successful career in New York, the perfect fiancé, and the perfect home location. However, things went downhill just before Christmas in which she was fired from her job as a PR executive with Lillah Sherwood’s firm and caught her fiancé cheating.

This led E.J to settle for a low paying job with a one-year time span where she was tasked with increasing the number of corporate retreats in Kalispell, Montana. With a population of 19,000, located hours from a large city Kalispell, Montana was initially, E.J’s worst nightmare. Fortunately, she soon came up with a great idea to make things work. The movie was criticized for being quite generic in the sense that such a story has been recycled a good number of times.

Also See: 5 Greatest Alisha Boe Movies Rated From Best To Worst

10. Cupid (2009)

Sean Maguire and Marguerite Moreau in Cupid (2009)
Sean Maguire and Marguerite Moreau in Cupid

The least on our compilation of Anna Chlumsky filmography is the Cupid series. For a fact, many shows get cut before they have room to mature, unfortunately, Anna Chlumsky happens to be featured in one of such shows. In as much as critics and fans alike gave Anna a thumbs down for her acting performance in this show, she might be excused. This is due to the fact that the story and general execution of the Cupid series wasn’t well-received by it’s intended audience hence the abrupt end with just 7 episodes. In the series, Anna played the role of Josie where she appeared in 4 episodes including; “My Fair Masseuse,” “Shipping Out,” “The Tommy Brown Affair,” and “The Great Right Hope.”

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