365 Days of Musical Theater: 31-45


Photograph of headphones, sideways, with the text 31 - 45

When I started my quest to tweet (and later, blog about) 365 musical theater songs, I told myself not to get too excited and use up all of my favorites in the beginning. A year is a long time. I promised myself I would spread out those Favorites (capital F for emphasis) so that they could be peppered in throughout the year for random bursts of pure joy…and I've been horrible at actually doing that.


You already saw in my last post (#16-30) that I dropped one of my favorites in for St. Patrick's Day. Well, in this edition, I feature four of my favorite male performers, the song that I think might be the greatest company number ever done, and a clip of a concert that sparked my obsession with singers performing songs from roles they would probably never play. I may have failed at holding back, but that means the selection featured in this post is one I really love. I hope you love it, too.


These songs were tweeted between March 25, 2022 and April 8, 2022.


All entries in my 365 Days of Musical Theater Series can be found here.


31. 'Giants in the Sky' from Into the Woods (Ben Wright as Jack)

Original Broadway Cast (1987-1989, this version aired on American Playhouse

in 1991)

I was too young to see Into the Woods during its original Broadway run, but I was the perfect age to watch the filmed incarnation regularly when it was released for public purchase. My favorite part was always when Jack (of beanstalk fame, who young me thought was gorgeous) sang 'Giants in the Sky,' his fast-paced number about the discoveries he made as a result of climbing the beanstalk and encountering the titular giants in the sky. When done well (or, perfectly, as I would argue Wright did it) it's like watching someone grow up right before your eyes. Watch here.


32. 'Solidarity' from Billy Elliot (Company)

Original London Cast (2005-2016)

It's hard for me to put into words how brilliant I found the staging for 'Solidarity' in Billy Elliot. Based on the film of the same name, about a young boy who develops a love for ballet at the same time as the miners in Thatcher England are going on strike, this song combines those two elements. On the one hand you have Billy at his dance classes discovering his potential and on the other you have the picketing miners. The choreography is magnificent and the song is extremely memorable. Listen here or watch a short clip of it from the Broadway production below to get an idea of the breathtaking visuals:


33. 'Soul of a Man' from Kinky Boots (Stark Sands as Charlie Price)

Original Broadway Cast (2013-2019)

My biggest failure in terms of spreading out my favorites was not keeping Stark's 'Soul of a Man' for later in the year. I intended to, because it is truly at the top of my favorite solo performances list. I've been a fan of Stark's since he made his Broadway debut in Journey's End and in 2012, my friend Danielle was kind enough to join me on a road trip to Chicago to see the pre-Broadway run of Kinky Boots. The show is a hopeful celebration of self-discovery and acceptance, and Stark's emotional solo 'Soul of Man' was, to me, exactly what musical theater should be. I've seen it many, many times live since then--because it moved to Broadway (and, by the way, Stark was among those Tony nominated for it.) I definitely planned to save posting about it for later, an exchange with my friend Louie caused me to be unable to resist indulging in sharing this performance any longer. It is the pinnacle of perfect musical theater for me, and I cannot stress enough just how special I think it is. Watch here.



34. 'I'm Alive' from next to normal (Aaron Tveit as Gabe)

Original Broadway Cast (2009-2011)

Aaron Tveit won a Tony Award for his role in Moulin Rouge last year, but I'll never be over the fact that he wasn't even nominated for his portrayal as Gabe, the son at the center of the family drama next to normal. I remember confidently putting him down as not only nominated, but winning, in my family's Tony predictions contest. Tveit expertly walked that fine line between charming and disturbing, giving Gabe all the layers he needs for the story to work (but you won't get spoilers from me), and flying around the multi-level set like it was nothing. It was truly spectacular to behold. This song has been a staple on my playlists for years, and I doubt it'll ever be removed. It definitely sits near the top of my favorite male performances list--which is why in my intro to this post I admitted that I failed to spread my favorites around as much as I'd intended. Watch here.



35. 'Role of a Lifetime' from bare: a pop opera (Michael Arden as Peter)

Original Off-Broadway cast (2004)

bare is the story of a young man named Peter who falls in love with Jason, a very popular student at their Catholic boarding school. Although Jason returns his feelings, when their relationship becomes public it has catastrophic results. When I saw it for the first time in a little Off-Broadway house attached to a courthouse, it grabbed me by the throat and didn't let go until I was weeping at the conclusion. 'Role of a Lifetime' comes early in the show, as Peter reflects on the hidden nature of their relationship and his concerns about the situation. I chose it because it's a great introduction to the show and Arden's performance is breathtaking. That said, the entire show (which has taken on multiple incarnations) has been released as an audio recording and as I believe the show is musically wonderful from start to finish, I highly suggest expanding just beyond this number (if you ever want to see me weep, just play the title song in my presence.) Listen here.

36. 'Life Upon the Wicked Stage' from Show Boat (Anna Kendrick)

My Favorite Broadway: The Leading Ladies (1998)

Following all those dramatic male songs, I felt the urge to change things up a bit. I wanted a female song that amused me. The first one that came to mind was a very young Anna Kendrick (Pitch Perfect) singing 'Life Upon the Wicked Stage' (an adult number) supported by the Kit Kat girls from the cast of Cabaret. This bundle of curiosities was part of the concert My Favorite Broadway: The Leading Ladies. As with Into the Woods, I did not attend this concert in person, but I did own the video recording of it. I view many of its performances as iconic and they were incredibly influential on me (one of the biggest was #42 in this very post), so you will see it pop up a few times as we go through this year. For now, though, enjoy a little fun. Watch here.



37. 'Stepsister's Lament' from Cinderella (Ann Harada as Charlotte + women's

ensemble)

Broadway cast (2013-2015)

I decided to follow up one piece of smile-making entertainment with another by featuring Ann Harada (one of the stage's great comedic actors and nicest people) as Cinderella's stepsister Charlotte. In this classic song she wonders (or rather, laments) that men go for women like Cinderella who are 'obviously unusual' and 'simply lovely' as opposed to a 'solid' and 'usual girl' like her. It's a fabulous moment for all the characters in life who aren't the ingénue. Listen here.


38. 'One Song Glory' from Rent (Will Chase as Roger)

Rent: Filmed Live on Broadway (2008)

Although this updated take on the opera La Bohème achieved legendary status with my generation very quickly, I was never a fan. Still, when Will Chase (who I adore) stepped into the role of Roger on Broadway at the tail end of 2005, I had to return. I ended up seeing it several times while he was there (it was worth it) and although I've never been converted to being a devotee like many people I know, two songs grew on me: 'One Song Glory' a ballad in which Roger contemplates his mortality and unfulfilled creative life and 'Santa Fe' a dreamier number sung primarily by the characters of Collins and Angel. To me, Rent isn't Rent without Will (even though, yes, I know he isn't the original) so I had to feature him as the representative of this 90s classic. Watch here.

39. 'She Loves to Hear the Music' from The Boy from Oz (Stephanie J Block

as Liza Minnelli)

Original Broadway Cast (2003-2004)

Quite understandably, most people remember The Boy from Oz for Hugh Jackman's award-winning turn as Peter Allen, but when I saw the show I left thinking about Stephanie J Block's spot-on performance as Liza Minnelli. So, for this day, I chose her big (and sparkly) solo number. Listen here.


40. 'This is Not Over Yet' from Parade (Brent Carver as Leo Frank, Carolee

Carmello as Lucille Frank)

Original Broadway Cast (1998-1999)

Parade is based on the true story of Leo Frank, the Jewish man in Georgia convicted of the murder of Mary Phagan a teen factory worker. He appealed this decision, but in 1915 he was taken by a mob and lynched. It was a series of events that caused major conversations around the country, including a focus on antisemitism. As you can imagine, it's not a happy musical. However, 'This is Not Over Yet' is, outwardly, a happy number: it occurs when an imprisoned Leo learns from his wife that his case will be re-examined and feels a surge of hope. It was recently announced that Michael Arden (who sings 'Role of a Lifetime', #35 on this list) will direct a special production of it this November, so it's the perfect time to revisit the original. Listen here or watch the Tony Awards performance of the song here.


41. 'Something's Coming' from West Side Story (Cheyenne Jackson as Tony)

San Francisco Symphony (2013)

One of my big musical theater confessions is that I've never really liked West Side Story. I've seen and heard many versions of it, but I've always felt the first half dragged too much for me to get invested in the second half. I usually mentally check out before intermission. I know this is blasphemy to many, but I can't help it, I feel how I feel! Even with shows I don't like, though (like with Rent above), there is usually at least one song I enjoy. In West Side Story, that song is 'Something's Coming.' It's a song that, when done by someone like Cheyenne Jackson, is boiling over with pure life, and I love that. Listen here.


42. 'Man of La Mancha' from Man of La Mancha (Linda Eder)

My Favorite Broadway: The Leading Ladies (1998)

I trace my obsession with singers performing pieces that they traditionally would not sing directly back to the moment young me saw Linda Eder sing 'Man of La Mancha' during the My Favorite Broadway: The Leading Ladies concert. Her performance shook my world and shifted my perspective...it also sparked my desire to be someone who sang a lot of songs that purists and traditionalists thought I shouldn't. She was one of the female singers whose work most influenced me when I decided to start voice lessons. No one will ever sing this song better than her in my mind. Watch here.



43. 'The Mad Hatter' from Wonderland (Kate Shindle as Mad Hatter)

Original Broadway Cast (2011)

Although Wonderland was technically a flop, I loved this spin on Alice in Wonderland. In particular, I loved the decision to make the Mad Hatter a woman with two powerful, awesome, show-stealing numbers. The first (which contains another thing I love: a plethora of very quick lyrics) is the one I chose for this. The other, darker, song is one you should also listen to - it's called 'I Will Prevail.' Kate Shindle's stunning costumes and dedication to a complex embodiment of this character who is traditionally male and occasionally Johnny Depp made it a performance that I adored, and it's still on my list of roles I'd love to play. Listen here.


44. 'Being Alive' from Company (Raúl Esparza as Bobby)

Company, filmed for Great Performances (2008)

When I was considering a song from Company it was difficult to choose which one, because the show (about a single person named Bobby/Bobbie who spends their 35th birthday surrounded by lots of friends who wonder when they will finally get married) is so rich in fantastic songs. In addition to 'Being Alive' I particularly also suggest watching Madeline Kahn's famous rendition of 'Getting Married Today.' But the reason I chose Raúl Esparza's 'Being Alive' was because Company, and Raúl's performance in particular, is very near and dear to the hear of one of my friends, so this one is for Deborah. Watch it here.


45. 'Fable' from The Light in the Piazza (Victoria Clark as Margaret)

Original Broadway Cast (2005-2006)

In 2005, my friend Jill and I developed an obsession with the musical The Light in the Piazza. While she was enamored with Kelli O'Hara's wonderful turn as Clara (a young woman with developmental disabilities due to a childhood injury who finds unexpected love on a trip to Italy) and wanted to sing all of her music, I was drawn to Victoria Clark's depiction of Margaret, Clara's mother. Clark eventually won the Tony for the role, and deservedly so in my book. Her 'Dividing Day' (about the crumbling of her marriage) is an underrated masterpiece, but I chose the song 'Fable' because it is a masterpiece of an 11 o'clock number that show tremendous character growth through self-reflection, and everyone should hear it. Listen here.



Happy listening! I'll be back soon with 15 more songs, including one from the musical production that I've seen the most, several based on historical events, and one that probably shouldn't even be on this list!


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