Welcome to 5 Favorites. Each week, I will put together a list of my 5 favorites (films, performances, whatever strikes my fancy) along with commentary on a given topic each week, usually in relation to a specific film releasing that week.

On the Friday after thanksgiving, one of the greatest lyricists of all time died at the age of 91. Stephen Sondheim has left an indelible impression on musical theater through his length career as a lyricist and as a composer. His creative energy is unmatched and his unparalleled influence will be felt for decades to come. This weekend, one of the handful of musicals he provided only lyrics to, West Side Story finds its way to the big screen once again after the Robert Wise/Jerome Robbins adaptation of 1961. That original film won 10 of the 11 Oscars for which it was nominated, becoming one of the all-time most honored films in Oscar history. It won Best Picture and history could repeat itself again this year.

Directed by Stephen Spielberg, the new adaptation has already received tons of praise and while the Academy has been loath to recognize remakes, sequels, and the like, Spielberg’s the kind of major director you don’t ignore. Can the film top the original’s 11 nominations. Will it be able to overcome the likes of Belfast and Dune in a number of head-to-head match ups? It’s hard to say, but we’ll find out in only a few months. That said, this week’s article is intended to look back at Sondheim’s theatrical legacy. While this is ostensibly a film-related website, Sondheim is one of my favorite theater geniuses.

What’s most interesting is that Sondheim has several intriguing connections to cinema outside the handful of works that have been adapted from stage to screen. In 1973, Sondheim co-wrote the screenplay to Herbert Ross’ The Last of Sheila with Anthony Perkins. Perkins had starred in an ABC Stage 67 production of Evening Primrose in 1966, a 1-hour show about a secret society of people who live in department stores, composed by Sondheim. Sondheim follows that up with a composing credit on Alain Resnais’ Stavisky in 1974 then as the composer for Warren Beatty’s Oscar-winning drama Reds in 1981. In between those composing projects, he wrote an original song for The Seven-Per-Cent Solution, the wonderfully bawdy “The Madame’s Song (I Never Do Anything Twice).” His next original song for the big screen came in Beatty’s 1990 film Dick Tracy. He wrote a whole slate of songs for the film, winning his only Oscar for the song “Sooner or Later,” sung in the film and on the Oscar stage by Madonna.

Three times previously have I looked at stage-to-screen adaptations in one way or another. In those lists, I’ve covered Company and Sweeney Todd before (which would be my two favorites of his), so I’ll actually leave them to the side this time around. I’ll also set aside West Side Story, Gypsy, and Do I Hear a Waltz, the three shows Sondheim only created the lyrics for, with composers Leonard Bernstein, Jule Styne, and Richard Rodgers respectively. That leaves 15 titles from which to select 5. That won’t be a problem either since there are only a handful of his stage musicals I either haven’t heard (Saturday Night, The Frogs, and Road Show) or didn’t like (A Funny Thing Happened on the Way to the Forum and Anyone Can Whistle).

That leaves eight titles to choose from. There are the five I chose below (numbers three through seven on my solo favorites list) and then three honorable mentions: Sunday in the Park George (for which he won a Pulitzer Prize), Into the Woods, and Passion. I like all three and they all have some all-time great songs in them, but they just weren’t quite the match for my selections. Here they are in chronological order.

Follies (1971)

Reminiscing about theatrical life during the era of the Ziegfeld Follies, Sondheim gave us a musical that celebrated Broadway’s long history while telling the story of revue veterans who join a reunion at a crumbling theater on the verge of demolition. The members of the Weismann’s Follies” have come together to discuss love, life, and recriminations over a slate of musical numbers.

Like the follies it references, the plot barely ties together an array of musical numbers into a cohesive plot surrounding two couples who met originally in the same theater years before. As they discuss through musical numbers whether they feel they have had the lives they once dreamed of or if they are miserable in their old age, other numbers are intermixed comparing modern times to the Depression-era period between World War I and World War II when the follies were at their height of popularity.

The show itself is something of a mixed bag. There are great numbers and mediocre numbers, but some of the best songs Sondheim ever wrote came from this act, including “I’m Still Here,” originated by Yvonne de Carlo (of Munsters fame), “Too Many Mornings,” and “Losing My Mind” among others. It’s a tuneful show that gives the audience a look back into the halcyon days of the Follies era through the jaded eyes of its performers.

A Little Night Music (1973)

Based on Ingmar Bergman’s film Smiles on a Summer Night, A Little Night Music took a classical music approach to the setting, a series of Swedish locales that surround a pair of former lovers who went on to lead separate lives. Fredrik Egerman (Len Cariou) is a successful lawyer recently married to an 18-year-old virgin, Anne (Victoria Mallory). Fredrik’s 20-year-old son Henrik (Mark Lambert) lives with them.

His ex-lover, Desiree Armfeldt (Glynis Johns), is back in town from her successful career as a touring actor. Her daughter Fredrika (Judith Kahan), a product of her tempestuous affair with Fredrik lives with Desiree’s mother Madame Armfeldt (Hermione Gingold), a former courtesan. She is now secretly courted by Count Carl-Magnus Malcolm (Laurence Guittard) who’s wife Charlotte (Patricia Elliott) must contend with his dalliances who encouraging her friend Anne to flaunt her youth in front of her husband in order to punish Desiree for her affair with her husband.

The show is filled with courtly intrigue and the orchestral score is a melodious construction. This is the show from which the legendary ballad “Send in the Clowns” originates, but it’s not the only great song in the show, others include “Now/Later/Soon,” “The Glamorous Life,” “Liaisons,” “Every Day a Little Death,” and “A Weekend in the Country,” all from Act 1. Act II has its own delights like “Send in the Clowns” and “The Miller’s Son.” It’s a wonderful show even if it’s one of his most deeply dramatic.

Pacific Overtures (1976)

Sondheim was never afraid of trying something new. This is the case with his 1976 musical Pacific Overtures, which is a historical drama looking back at the 19th-Century westernization of Japan and the successes and failures that followed. In the original production, Oscar nominee Mako (1966’s The Sand Pebbles) takes the lead in a play that combines Japanese musical and theatrical styles with an American aesthetic, thematically connecting the show’s narrative.

While the show didn’t produce any songs that most audiences would instantly remember, songs like “Four Black Dragons” and “Chrysanthemum Tea” are fascinating for their creative use of lyrics while the bawdy “Welcome to Kanagawa” is a humorous look at geishas. Then there’s “Pretty Lady” and “Poems,” two emotion-filled songs that have vastly different outcomes. It’s a beautiful and melodic piece even if it’s seldom cited as one of Sondheim’s best, even though it is.

Merrily We Roll Along (1981)

Sondheim was well known for both subverting expectations and tinkering with the successful format of traditional musical theater. Merrily We Roll Along is one such play as it looks at a trio of longtime friends who go into business together writing hit musical theater, but as they arrive at their class reunion, they begin reflecting back on the road that brought them where they are and whether their friendship could truly survive all that it went through.

This production was one of the shows that Sondheim used to take jabs at the industry and its product-for-profit model. While something like Sunday in the Park with George was more adoring in its reflection on art, Merrily was full-throated in its anti-capitalist views of the process of creating art. He also took to task his critics who sometimes claimed he never wrote “hummable” melodies. It’s interesting to note that the song in which that rebuke occurs is a perfectly hummable one on its own.

Since many of the tunes in the show are vignettes, it’s sometimes difficult to settle on one song being better than another. The company singing of “Merrily We Roll Along” is a neat interstitial that reflects a similar use of such a device in Sweeney Todd while “Not a Day Goes By” and “Old Friends,” and especially its reprise, are lovely songs that capture a wistful tone of the show’s characters while the opening “Hills of Tomorrow” sets the mood of hopefulness that evaporates as the show progresses. Then there’s the smart-alecky “Bobby and Jackie and Jack” one of the most humorous numbers in the show.

Assassins (1990)

When you want to talk about the ways Sondheim reconfigured how audiences saw musical theater, Sweeney Todd is a good example, taking a horrific situation and turning it into a rousing production. Assassins does something similar, but it manages to be even more illuminating. It’s not in the way it frames various presidential assassins or attempted assassins throughout United States history, but in how it presents these individuals as taking inspiration from one another and the strange devotion some have to celebrating the macabre, especially assassins.

Using the framing device of a dark carnival atmosphere, the various villains of the piece play wicked games of chance while reflecting on their own sordid entries in political history. At the heart of the show is John Wilkes Booth who inspired numerous copycats throughout history and who, in a meditative scene late in the show, helps Lee Harvey Oswald prepare for his potential assassination of John F. Kennedy.

What’s most captivating about the show is not that it absolves any of these figures of their horrible contributions to history, but in its discussion of how such figures latch onto ludicrous ideal to justify their actions and simultaneously castigates the audience for taking any vicarious joy from such. It also features some remarkably amazing juxtapositions of traditional musical song styles with the disturbing reactions of its characters.

The most fascinating example is the love song featuring attempted Reagan assassin John Hinckley and Squeaky Fromme who tried to kill Gerald Ford. The pair don’t sing of their love for one another, but for their respective love of the figures who they thought encouraged them to attempt those assassinations. Jodie Foster in the case of Hinckley and Charles Manson in Fromme’s case. The show also produced other fantastic creations such as “The Ballad of Booth,” “November 22, 1963,” and “Everybody’s Got the Right,” which bookends the show. It’s not your traditional stage musical, but it’s certainly an intense and entertaining one, in a morbidly humorous way.