When a night opens with surprise guest Lin-Manuel Miranda, you’d better buckle up. Two-time Tony Award winner Jason Robert Brown celebrated his milestone 50th SubCulture residency concert with a one-night-only benefit performance to support Brady, “the national organization uniting gun owners and non-gun owners alike in the comprehensive solutions that will end the gun violence epidemic in this country.”

Brown dedicated the evening to a program filled with Sondheim tunes—as well as songs from his own repertoire—culminating in the moment when Sondheim himself joined Brown onstage at the piano for some play and conversation.

“I never wanted to write for anything but the theatre,” Sondheim revealed. And though he performed in college (his favorite role the serial killer lead in Night Must Fall), he never dreamed of performing. “I’m always perfect in my living room.”

Here are nine highlights from an evening of sensational moments.

1. Lin-Manuel Miranda Shocks the Audience With His Appearance
After introductions from executive producer Marc Kaplan and Brady president Kris Brown, Jason Robert Brown took the mic to explain a bit about his residency and the root of Sondheim as a creative inspiration in his life, citing that he’d played Charley in his French Woods production of Merrily We Roll Along. And sure, Lin-Manuel Miranda may have done it at City Center, but “I’ve been rehearsing this song for the past 33 years, since I was 16.” Brown began Charley’s big solo, and midway through the song Miranda burst out of the wings and the two completed the song as a duet. Two real life Charleys.

2. That Orchestra
While a small band consistently backs Brown at SubCulture downtown, the June 24 concert featured a 16-piece orchestra conducted by Georgia Stitt. In the second number of the show, “Melinda” (on Brown’s album how we react and how we recover) the audience got a taste of what this band is capable of with the lush sound and soloists. Brown also wrote new arrangements to a number of Sondheim tunes, including “Move On.”

3. Katrina Lenk’s “Last Midnight”
As a featured guest, Lenk sang five songs—a mix of Brown and Sondheim tunes. Brown first encountered Lenk during the Off-Broadway Atlantic Theatre Company run of The Band’s Visit and thought, “How did [David] Yazbek find her?” Her mesmerizing quality was best put to use in her rendition of “Last Midnight” from Into the Woods. Her wry demeanor, her powerful mix, and her severity made it an unforgettable performance.

4. “Move On”
Time stopped when Joshua Henry and Lenk entered the stage to duet on a newly orchestrated version of the duet from Sunday in the Park With George. Henry’s richness coupled with Lenk’s fragility equaled brilliance.

5. Shoshana Bean’s Acting
Brown’s residency originated from a single concert with his “favorite voice on the planet” Shoshana Bean. The two needed a space for a concert in August 2014 and SubCulture was the only available spot; five years later, Brown hasn’t left. The two dueted on “The Next Ten Minutes” from The Last Five Years and Bean transported the audience into the story of a marriage locked in a moment of bliss before it was destined to end. She became Cathy in that moment, and the audience was transfixed.

6. Rob McClure Sang Sondheim’s Favorite Jason Robert Brown Song
In their ongoing relationship, Brown discovered that Sondheim’s favorite song of his is “I Love Betsy” from Honeymoon in Vegas. “That’s the one?” Brown recalled in astonishment. The original star of the short-lived Broadway show, Rob McClure, took to the stage to reprise his opening number, bringing pure delight to the song about his one true love.

7. Sondheim’s Solo
When Sondheim took the stage, the audience greeted him with a standing ovation and then he simply sat and played…and sang. Accompanying himself on piano, Sondheim sang a delicate rendition of “Good Thing Going” from Merrily We Roll Along to an awed house.

8. The Harmonic Structure
The evening wasn’t all song. Brown helped the audience get to know the real Stephen Sondheim a bit better in a casual conversation about his transition from acting in college to songwriting. The two composer-lyricists agree that a writer’s harmonic structure is as individual as a fingerprint. To prove it, Brown sent Sondheim a single line piano melody—no tempo, no rhythms, no harmonies—and said “you harmonize this.” First, Brown played us his actual harmonization of “It’s Hard to Speak My Heart” from Parade, followed by the short isolated melody so the audience could hear what Sondheim received. Then, Sondheim played his harmonic treatment of the melody; it sounded like a cut song from Company, something undoubtedly Sondheim. The Town Hall audience earned a rare glimpse at the creative process and workmanship of two artists.

9. Piano-Only Duet of “Not While I’m Around”
Simplicity is often best. Brown and Sondheim played piano together while Lenk sang the touching ballad from Sweeney Todd.

Full set list:
“Franklin Shephard, Inc.” from Merrily We Roll Along featuring Brown and Lin-Manuel Miranda
“Melinda”
“Children and Art” from Sunday in the Park With George
“Another Life” from The Bridges of Madison County featuring Katrina Lenk
“Cassandra” from The Connector featuring Katrina Lenk
“Last Midnight” from Into the Woods featuring Katrina Lenk
“Song About Your Gun”
“Nothing’s Bigger Than Kong” from a workshopped version of King Kong by Brown and Marsha Norman
“I Love Betsy” from Honeymoon in Vegas featuring Rob McClure
“The Next Ten Minutes” from The Last Five Years featuring Brown and Shoshana Bean
“Move On” from Sunday in the Park With George featuring Katrina Lenk and Joshua Henry
“Good Thing Going” from Merrily We Roll Along featuring Stephen Sondheim
An exercise in melody and harmony featuring Stephen Sondheim
“Not While I’m Around” from Sweeney Todd featuring Katrina Lenk
“Wait ’Til You See What’s Next”
Encore: “All Things In Time”

The orchestra, conducted by Georgia Stitt, featured pianist and percussionist James Sampliner, guitarists Gary Sieger and Justin Goldner, bassist Randy Landau, percussionist Jamie Eblen, woodwinds Kristy Norter and Robert DeBellis, trumpeter Tony Kadleck, trombonist Jenn Wharton, violinists Todd Reynolds, Katherine Livolsi-Landau, Louise Owen, violinist/violists Monica Davis and Orlando Wells, and cellists Mairi Dorman-Phaneuf and Adele Stein, as well as background vocalists Adee David and Anastasia Talley.

Executive produced by Marc Kaplan, the concert was directed by Daisy Prince with lighting design by Zach Pizza and sound design by Jon Weston.