Mashups of songs are a lot of fun. You take two songs with similar themes (or perhaps opposing viewpoints) and splice them together to create a richer experience for how they compliment one another. They did this a lot on the TV show Glee, but the idea has been around much longer than that, and employed to great effect. 

Mashups of Broadway showtunes are clever way to elaborate on the message of one song, by adding an additional layer of thinking with that second song. The first one that I encountered was the combination of “With You" from Pippin and "Gifts of Love" from The Baker's Wife, sung gloriously by Marin Mazzie for the sumptuously produced The Stephen Schwartz Album. While on a long road trip a few weeks ago, I listened to that album and started getting some ideas of other Broadway mashups I'd like to hear. Here are some of the ideas for songs that I think would make amazing pairings. 

"Hold On" from The Secret Garden
and
"Let it Go" from Frozen

 The musical The Secret Garden is full of haunting songs of melancholy, hope and fear by Lucy Simon and Marsha Norman. The Act Two showstopper “Hold On” is sung by the maid Martha to a little orphan girl named Mary Lennox who is wrestling with a multitude of fears. With its metaphoric imagery of outlasting the storm, I was inspired to think of how this piece could marry with Frozen’s “Let it Go.” The Kristin-Anderson Lopez and Robert Lopez song is about reclaiming strength, rising from the ashes and shunning the horrible weather. “The cold never bothered me anyway.”

"The Sun Won't Set" from A Little Night Music
and
"Tonight" from West Side Story

 A Little Night Music features the delightful ditty “The Sun Won’t Set”, with an amusing and sophisticated lyric by Stephen Sondheim about the tension caused when the day refuses to end. What better song to pair it with than “Tonight” from West Side Story, this time with a Sondheim lyric that pleads for an endless day to become and endless night. The irony of the two together would make for clever combination, and weaving in and out of the intoxicating Sondheim and Bernstein melodies would also add to the fun.

"Goodnight, My Someone" from The Music Man
and
"Good Morning, Starshine" from Hair

 The Music Man has myriad charms, and one of its best is the gentle little torch song “Goodnight, My Someone” that grows out of a piano scales exercise. Meredith Willson composed music and lyrics for a pining music teacher to sing to the night sky as she wishes upon a star. This perspective of wishing on the night sky would neatly juxtapose with “Good Morning, Starshine” from the musical Hair, a song about greeting the morning sky and celebrating a new day. Galt MacDermot’s gentle but rolling melody would butt up against Willson’s song nicely.

"Corner of the Sky" from Pippin
and
"A Piece of Sky" from the film Yentl

 The sky is the limit on this one (I know, groan), but before you dismiss my idea, I think these songs would be great together. “Corner of the Sky” from Stephen Schwartz’s score for Pippin, is a soaring “I want” song for a young man searching for his purpose in life. “A Piece of Sky”, by Michel Legrand and Alan & Marilyn Bergman, is an inspiring and uplifting piece in a similar vein, but for a young man searching for her place in the world.  

"There's a Fine, Fine Line" from Avenue Q
and
"Time Heals Everything" from Mack and Mabel 

One of my favorite showtunes to come out of the last twenty years is “There’s a Fine, Fine Line” from Avenue Q. Never has the challenges of navigating the uncertainty of a relationship been better captured than in this Jeff Marx/Robert Lopez song…unless, of course, you look at Jerry Herman’s expert thesis on the same theme, “Time Heals Everything” from Mack & Mabel. Double the angst and double the hurt will make this mashup the ultimate break-up song.

"Nothing is Too Wonderful to Be True" from Dirty Rotten Scoundrels
and
"Old Devil Moon" from Finian’s Rainbow 

The moon has a way of finding it’s way into many showtunes, often having a magical influence on love. “Nothing is Too Wonderful to Be True”, the tentative, subtle torch song by David Yazbek from Dirty Rotten Soundrels makes several references to the moon’s effects. Pair the song with the more brazen and bewitching“Old Devil Moon” from Finian’s Rainbow, music by Burton Lane and lyrics by E.Y. Harburg, and you are in for a song that explores the full range of the moon’s potential effects.

"Ribbons Down My Back" from Hello, Dolly!
and
"Lazy Afternoon" from The Golden Apple

 The idea of this pairing makes me weak in the knees that’s how lovely I think these two songs would be together. Jerry Herman’s “Ribbons Down My Back” may arguably be the perfect showtune, economically and poetically setting up the situation, mood, time and place. It’s a simple wish for love in the summertime. That’s why I think it combines perfectly with “Lazy Afternoon” from The Golden Apple. Jerome Moross (music) and John Latouche (lyrics) create a bucolic ballad that simply invites the listener to join them for a quiet, summer afternoon.  

"It's Today" from Mame
and
"The Party's Over" from Bells Are Ringing

This is not a difficult combination to imagine: the first song is about celebrating life with a party, the second song is about the party coming to and end. The Jerry Herman song from Mame is fizzy and full of energy. The Jule Styne (music) and Betty Comden /Adolph Green(lyrics) from Bells are Ringing is reflective and somber. Together, they mashup into a spectrum of the good and the bad.

"Life Upon the Wicked Stage" from Show Boat
and
"Welcome to the Theatre" from Applause 

Finally, how about two great songs about the theatre, mashed together to create an ultimate song for celebrating the TRUE diva experience. “Life Upon the Wicked Stage” from Jerome Kern’s and Oscar Hammerstein’s Show Boat, is all about the unglamorous life of an actress and people’s illusions about the life of a performer. Charles Strouse’s and Lee Adam’s “Welcome to the Theatre” from Applause explores similar diatribes against the theatrical life. Both are slightly bitter, wisecracking, and they resonate on a deeper level when you consider the loneliness being shared in each song. Put them together and it becomes an epic monologue about how our dream become harsh realities.