Set in turn-of-the-century New England, the musical tells the story of orphan Jerusha Abbott of the John Grier Home and her mysterious benefactor who agrees to send her to college, who she dubs "Daddy Long Legs" after seeing his elongated shadow.

The musical was developed as part of the Ann Deal/Fashion Forms Plays-in-Progress Series at Rubicon Theatre in Ventura County, California in 2007.

Workshop readings for the musical were done at the Rubicon Theatre Company as early as 2008, with Leslie Henstock as Jerusha and Robert Adelman Hancock as Jervis.

Producers Ken Davenport and Michael Jackowitz presented a private New York industry reading of the musical on January 24, 2014, with McGinnis and Hancock reprising their roles.

In addition to the original creative team, the production has sound design by Peter Fitzgerald, lighting adaptation by Cory Pattak, and musical direction, arrangements, and orchestration by Brad Haak.

The role of Jervis was temporarily played by understudy Will Reynolds from October 29 to November 19, after Nolan's departure to join the company of Bright Star.

[17] The production was co-premiered by the Rubicon, TheatreWorks Silicon Valley at the Mountain View Center for the Performing Arts in Mountain View, California from January 20 until February 14, 2010;[18] (extended through February 21),[7] and Cincinnati Playhouse in the Park from March 13 until April 10, 2010;[19] in what was called as a "rolling world premiere," due to the various changes continually made to the show on the road.

TheatreWorks Silicon Valley participated in the New York casting, and built the sets, props, and costumes, which were shipped to Rubicon for the initial performances.

Several stagings featured Ephie Aardema, Christy Altomare and Penny McNamee as Jerusha and Kevin Earley as Jervis.

Directed by Connor Clarke Nominated for Best Musical - Matilda Awards 2019 and Ella Macrokanis was nominated for the Billy Brown Award -Best Emerging Artist 2019 The Japanese premiere of the production opened at the Theatre Creation in Tokyo from September 2–19, 2012, and toured to theatres in Niigata, Oita, Osaka and Fukuoka where it closed on October 3, 2012.

The Canadian premiere of the production, starring McGinnis and Hancock, opened at the Royal Manitoba Theatre Centre Mainstage in Winnipeg, from March 14 until April 6, 2013.

[35] The Russian premiere of the production made into Dear Mr. Smith opened at the Theatre "Shelter of Comedians" in Saint Petersburg June 4–6, 2021.

On her way there, she glimpses one of the Trustee's long, spindly, and spidery shadow cast by the headlights of his awaiting car ("The Oldest Orphan in the John Grier Home").

After musing over what she'll call her mysterious benefactor, she finally decides on "Daddy Long Legs" due to his tall figure and she imagining him to be old and gray ("Mr.

During the Christmas vacation, Jerusha stays behind in the college to catch up on her reading, and sends her love to Daddy Long Legs in her loneliness.

She becomes ill and writes angrily to Daddy Long Legs, accusing him of not caring for her and simply supporting her merely out of charity.

The summer arrives, and Jerusha begs Daddy Long Legs not to send her back to the John Grier Home, as she has nowhere to go to.

Jervis, adopting another guise as a "secretary" to Mr. Smith, sends her to Lock Willow Farm, where she explores her talent as a writer.

Jervis, through his secretarial alias, insists that she spend the summer at Lock Willow Farm instead due to his fear of Jerusha falling in love with Jimmy.

Feeling alone and trapped, Jerusha writes an angry letter in response to his domineering nature and finds it hard to forgive Mr. Smith ("I Couldn't Know Someone Less").

Despite Mr. Smith's warnings, Jerusha proceeds to Camp McBride due to some negative remarks she received from Jervis when he found out she turned down an invitation to Paris from Julia, to work as a teacher in French and algebra to support herself.

She then tells him that she will continue to repay her debt to him, and all future royalties will proceed to the John Grier Home, making her a trustee and therefore, meeting him at last.

Distressed over this revelation, as well as realising that he has read her private letters about him, Jerusha accuses him of playing with her feelings and the mere fact that he didn't even write back over the course of four years, which Jervis acquiesces to ("I'm A Beast (Reprise)").

[39] Alexis Soloski, reviewing the Off-Broadway production for The New York Times, found that Gordon's music and lyrics "have a charm and ease, though the songs can blur into one another in ways that are sometimes purposeful and sometimes not" and Caird's book "appealing" and direction "nimble."

He wrote of McGinnis to be charming, despite the "baldly expository opening number ('The Oldest Orphan in the John Grier Home')" and of Nolan to be "sweetly sympathetic here as he was harshly disruptive in Zhivago.