Teachout was born in Cape Girardeau, Missouri, the son of Evelyn (Crosno), a secretary, and Herbert H. "Bert" Teachout, a hardware salesman. He grew up in Sikeston, Missouri. He attended St. John’s College in Annapolis, Maryland; William Jewell College in Liberty, Missouri; and the University of Illinois at Urbana-Champaign. He lived in Kansas City from 1975 to 1983, working as a jazz bassist and writing about classical music and jazz for the Kansas City Star. He moved to New York City in 1985, working as an editor at Harper's Magazine (1985–87) and an editorial writer for the New York Daily News (1987–93) and as the News' classical music and dance critic (1993–2000). In 2004 he was appointed by President Bush to the National Council on the Arts, the advisory and review panel of the National Endowment for the Arts, completing his term in 2010. In 2005 he was hospitalized with congestive heart failure, but subsequently recovered. A political conservative with wide-ranging cultural interests and sympathies, he maintains cordial relationships with artists, critics, and bloggers from all parts of the political spectrum.
Teachout's latest book, Duke: A Life of Duke Ellington, which was published by Gotham Books on October 17, 2013, was longlisted for the National Book Awards nonfiction prize. He received a Guggenheim Fellowship for 2012 to support its completion. Parts of Duke and Satchmo at the Waldorf, Teachout's first play, were written at the MacDowell Colony in the summer of 2012. James Gavin, writing in the New York Times Book Review, called Duke a "cleareyed reassessment of a man regarded in godlike terms" that "humanizes a man whom history has kept on a pedestal", praising its "sound scholarship and easy readability." Kirkus Reviews called it “an instant classic…Teachout solidifies his place as one of America’s great music biographers.” Publishers Weekly called it “revealing…Teachout neatly balances colorful anecdote with shrewd character assessments and musicological analysis.”
Satchmo at the Waldorf, a one-man-two-character play about Louis Armstrong and Joe Glaser, Armstrong's manager, was premiered at Orlando Shakespeare Theater's Mandell Theatre in Orlando, Fla., on September 15, 2011, in a production starring Dennis Neal and directed by Rus Blackwell. An extensively revised version of Satchmo at the Waldorf in which Miles Davis is also briefly portrayed was produced by Shakespeare & Company of Lenox, Mass., in August 2012, with John Douglas Thompson playing Armstrong, Glaser, and Davis. The production, which transferred to Long Wharf Theatre of New Haven, Conn., in October 2012, and to Philadelphia’s Wilma Theater in November 2012, was directed by Gordon Edelstein. The Boston Globe described the revised version of the play as a "tour de force…Aided by director Gordon Edelstein and the consummately skilled Thompson as interpreter, Teachout—in his debut as dramatist rather than drama critic—has contributed a work of insight and power." According to the New York Times, "Reviewing a play is one thing; writing a play is quite another. Terry Teachout, drama critic for The Wall Street Journal, makes this hat-switching look far easier than it is with his first play…Mr. Teachout has done a fine job of building a fiction-plus-fact theater piece."
Satchmo at the Waldorf transferred to New York's Westside Theatre, an off-Broadway house, on March 4, 2014. It closed there on June 29, 2014, after 18 previews and 136 performances. According to The New Yorker, "Teachout, Thompson, and the director, Gordon Edelstein, together create an extraordinarily rich and complex characterization. The show centers on the trumpeter’s relationship with his Mob-connected Jewish manager of more than thirty-five years, Joe Glaser. Thompson forcefully inhabits both men—and throws in a chilling Miles Davis—delivering an altogether riveting performance." Thompson won the 2013–14 Outer Critics Circle Award and Drama Desk Award for "Outstanding Solo Performance" for his performance in the play. It was produced at the Wallis Annenberg Center for the Performing Arts in Beverly Hills, Ca., in May 2015, and at Chicago's Court Theatre, Colorado Springs' Theatreworks, Palm Beach Dramaworks, the Seacoast Repertory Theatre of Portsmouth, N.H., and San Francisco's American Conservatory Theatre during the 2015–16 season. It was produced by New Venture Theatre of Baton Rouge, La., Triangle Productions of Portland, Ore., B Street Theatre of Sacramento, Calif., and the Mosaic Theater Company of Washington, D.C., during the 2016-17 season and will be produced by the Alley Theatre of Houston in March of 2018. The Palm Beach Dramaworks production was directed by Teachout in his professional debut as a stage director. An acting version of the play is published by Dramatists Play Service.
Teachout's second play, Billy and Me, a four-character-three-actor play about the relationship between William Inge and Tennessee Williams, will be premiered at Palm Beach Dramaworks in West Palm Beach, Fla., on December 8, 2017.
Teachout's previous book was Pops: A Life of Louis Armstrong (2009, Houghton Mifflin Harcourt; JR Books Ltd in the UK, Larousse in Brazil, United Press/Alpina in Russia). "With Pops, his eloquent and important new biography of Armstrong, the critic and cultural historian Terry Teachout restores this jazzman to his deserved place in the pantheon of American artists," Michiko Kakutani wrote in her New York Times review of Pops. The Washington Post chose Pops as one of the ten best books of 2009, The Economist chose it as one of the best books of the year, and the New York Times Book Review chose it as one of the "100 notable books" of 2010.
Teachout has also written the libretti for three operas by Paul Moravec: The Letter, an opera based on the 1927 play by W. Somerset Maugham that was premiered on July 25, 2009, by the Santa Fe Opera; Danse Russe, a one-act backstage comedy about the making of Igor Stravinsky's The Rite of Spring that was premiered by Philadelphia's Center City Opera Theater on April 28, 2011; and The King's Man, a one-act companion piece to Danse Russe about Benjamin Franklin and his illegitimate son William that was premiered by Louisville's Kentucky Opera on a double bill with Danse Russe on October 11, 2013. In addition, Teachout was the librettist for Moravec's cantata "Music, Awake!," which was premiered at Rollins College by the Bach Festival Society of Winter Park (Florida) on April 16, 2016.
Teachout's other books include All in the Dances: A Brief Life of George Balanchine (2004, Harcourt), A Terry Teachout Reader (2004, Yale University Press), The Skeptic: A Life of H.L. Mencken (2002, HarperCollins), and City Limits: Memories of a Small-Town Boy (1991, Poseidon Press). He is the editor of Beyond the Boom: New Voices on American Life, Culture, and Politics (1990, Poseidon Press, introduction by Tom Wolfe) and Ghosts on the Roof: Selected Journalism of Whittaker Chambers, 1931–1959 (1989, Regnery Gateway). In 1992 he rediscovered the manuscript of A Second Mencken Chrestomathy among H.L. Mencken's private papers and edited it for publication by Alfred A. Knopf (1995).
He wrote the forewords to Paul Taylor's Private Domain: An Autobiography (1999, University of Pittsburgh Press), Elaine Dundy's The Dud Avocado (2007, New York Review Books Classics), William Bailey's William Bailey on Canvas (2007, Betty Cuningham Gallery), and Richard Stark's Flashfire and Firebreak (2011, University of Chicago Press) and contributed to The Oxford Companion to Jazz (2000, Oxford University Press), Field-Tested Books (2008, Coudal Partners), and Robert Gottlieb's Reading Dance (2008, Pantheon). He also appears in Alex Gibney's Sinatra: All or Nothing at All (2015) and two film documentaries about dance, Mirra Bank's Last Dance (2002) and Deborah Novak's Steven Caras: See Them Dance (2011).
Teachout contributed notes on recordings by Louis Armstrong, Gene Krupa and Oscar Peterson to Jazz: The Smithsonian Anthology (2011) and has written liner notes for CDs by jazz musicians Karrin Allyson, Gene Bertoncini, Ruby Braff and Ellis Larkins, Julia Dollison, Jim Ferguson, Roger Kellaway, Diana Krall, Joe Mooney, Marian McPartland, Mike Metheny, Maria Schneider, Kendra Shank and Luciana Souza, the pop-jazz Lascivious Biddies, the bluegrass band Nickel Creek, the Alec Wilder Octet, and the classical ensembles Chanticleer and the Trio Solisti, as well as for the original-cast album of Hands on a Hardbody.
Teachout won the Bradley Prize in 2014.