[1][2] It includes duet with Josh Groban, Neil Patrick Harris, Leslie Odom Jr, Loren Allred, Kelli O'Hara, Kate Baldwin, and featured Sting and appearances from Kristin Chenoweth, Lin-Manuel Miranda and many more.

[8] In October 1999, he sang as part of a vocal quartet for the opening of a new US Embassy in Ottawa, Ontario for then President Bill Clinton and Prime Minister of Canada Jean Chrétien.

[6][14][15] Estabrooks was the baritone soloist in Brahms' Eine Deutsches Requiem with Coro Vivo Ottawa in 2008[16] and has also performed with the Kennett Symphony of Chester County[17] and the Aldeburgh Connection[18] recital series.

[24][25] He made his Toronto Symphony Orchestra debut on October 9 and 10, 2012 with conductor Steven Reineke in a program entitled "Some Enchanted Evening: The Music of Rodgers & Hammerstein" with Broadway stars Ashley Brown and Aaron Lazar.

[28] He appeared as the Baron in the Opera Lyra Ottawa production of La Traviata on March 21 and 23, 2013 with the National Arts Centre Orchestra and Corrine Winters, Eric Magiore, Marion Newman, Gregory Dahl and conductor Tyrone Paterson.

[31] In March 2015, he made his debut with the Seattle Symphony with conductor Steven Reineke in a program titled Some Enchanted Evening: A Rodgers & Hammerstein Celebration with Broadway stars Ashley Brown and Aaron Lazar.

[citation needed] Participating artists included Annie Golden, Chris Mann and Peter Hollens; Broadway stars Telly Leung, Lexi Lawson, Liz Callaway, Ektor Rivera, Bryan Terrell Clark (Hamilton), Lillias White, Aaron Lazar, Ashley Brown, Carmen Cusack, Cass Dillon, Lauren Jelencovich (Yanni Vocalist), and Noah Stewart; spoken word artists Taylor Mali, Trace DePass, and Shanelle Gabriel; cabaret stars Natalie Douglas and KT Sullivan; and a pop chorus of 50 accompanied by full orchestra.

In October 2019, Estabrooks created the role of Mat Burke in the world premiere production of Anna Christie, a music drama based on the Eugene O'Neill play.

Artists included Emmy nominee Laverne Cox, Pulitzer Prize finalist Anna Deavere Smith, J'Nai Bridges, Harolyn Blackwell, Martina Arroyo, Simon Estes, Damien Sneed, George Shirley, Measha Brueggergosman, Krysty Swann, Karen Slack, Chauncey Packer, John Holiday, Audrey DuBois-Harris, Sidney Outlaw, Justin Austin, Brandie Sutton, and Russell Thomas, plus Norman's family and students from the Jessye Norman School of the Arts.

[37] On June 14, 2024 it was announced that broadway star Aaron Lazar, recently diagnosed with ALS, would release a star-studded album entitled Impossible Dream after the idea was proposed to him by Estabrooks.

Produced by Kitt Wakeley, himself, Aaron Lazar, Christina Giacona, David Das and Patrick Conlon, it was released on August 23, 2024 featuring duets with Lazar and a who's who of Broadway stars—including Josh Groban, Kelli O’Hara, Leslie_Odom_Jr., Neil Patrick Harris, Kate Baldwin, Norm Lewis, Loren Allred and joining them on the title track are Kristin Chenoweth, Brian Stokes Mitchell, Sting, Lin-Manuel Miranda, and more than 50 other performers.