 If you liked
Kaleido Star
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 ...then you might like
Glass no Kamen (2005)
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These two shows are extremely similar, both focusing on a teenage girl with a big dream and trying to make it. The only difference is that in Kaleido Star they focus more on things like gymnastics and dancing, while in Glass Mask it's about acting.
To reach one's dream, one's goal. Many obstacles stand in their way, but they forever push on.
Kaleido Star is an ever optimistic series, whose clear message is to keep trying and aim for their dreams. Sugary and upbeat, little kids will love it, but it's not too much that older people can't watch it.
Glass Mask (2005) is an adaptation of a famous (at least in Asia) 70's manga, set to a more modern setting. Less upbeat, and much more dramatic than Kaleido Star, but it's the same "reaching for their goal" genre. Probably appeal to more older fans, but most people will enjoy both.
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Both of these girls are willing to follow their dreams through any obstacle!
Both are good animes with solid drama, adventures of 2 girls who tried their best to fulfill their dreams, sharing their tough and happy times.
Both girls found not only their dreams but also their precious friendships, and a bit of romance. Although they belong to shoujo in genre, it's recommended to all audience.
We watch our main characters (Sora and Maya) start their journey into entertainment. For Sora, it's the circus-like Kaleido Stage. For Maya, it's taking the theater and acting world by storm.
Watching Glass Mask immediately invoked Kaleido Star for me, which I had watched years ago. Both series follow a similar structure - moving from play to play in Glass Mask, and from stage to stage in Kaleido Star, with lots of character drama and personal growth in between.
Both series are from the early/mid-2000s and invoke the same nostalgic feelings I have for the era. They also have similar running-lengths that are hard to find nowadys
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The concept of a dream and hoping to make themselves a superstar in the entertainment industry is a prominent theme in both Glass no Kamen (Glass Mask) and Kaleido Star.
Throughout both series, both main female protagonists strives to make their dream a reality. It's not easy and they face obstacles, rivals, and competitions. There is a sense of beauty present in both series that is artistic in the way their performances are done.
There is also solid drama in both series that often involves competing to be the best.
Both animes are about a girl who wants to accomplish he ultimate performance. In glass mask the main character grow as an actor under the guide of an former actress to accomplish and become the crimson goddess, while in Kaleido star the main character has guide from the spirit of the stage to perform the legendary stunt the Angel's Maneuver. Both main characters has challenges and a friend they compete with and support.
Because of the similar premise and overall feeling.
I watched Kaleido Star first and always thought that Glass Mask was like KS, but with acting instead of acrobatics. The stories of Kaleido Star and Glass Mask feature a female protagonist chasing their dream of being on the big stage in the entertainment world. Though they soon find out that becoming a performer brings many challenges and hardships that talent and hard work alone can't easily overcome.
Both KS and GM are slice of life/work life dramas, that share familiar themes and other elements such as comedy, conflicts, friendships, rivalries, and more; making both shows feel very
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