Some seasons on Broadway leave one show the clear frontrunner and eventual winner of a pile of Tonys, but sometimes multiple beloved and legendary shows—and performances—end up going head to head, and nobody knows who will win until the open the envelope on Tony night. From A Chorus Line versus Chicago to Ethel Merman versus Mary Martin and Ragtime versus The Lion King, we’re taking a look at some of the Tony Awards’ most hotly contested races.

1960 - The Sound of Music vs. Fiorello! versus Gypsy

It’s incredible now to think that in one season, Broadway saw the openings of The Sound of Music, Fiorello! and Gypsy, all of which continue to be regarded as legendary musicals in their own right. At the Tony Awards that year, The Sound of Music tied with Fiorello! for the title of Best Musical—the only time there’s been a Best Musical tie, by the way. Mary Martin, up against Ethel Merman’s now-iconic and legendary performance as Mama Rose, came up victorious as Best Leading Actress in a Musical. Meanwhile, Fiorello! went on to win the Pulitzer Prize for drama but has never been seen on Broadway since; The Sound of Music superseded its popularity on stage with a screen adaptation starring Julie Andrews that remains one of the most beloved movie musicals to date; and, Gypsy has received no less than four successful Broadway revivals, with a fifth rumored to be heading our way soon by way of London’s West End.

The competition was fierce that season for a lot of reasons. Mary Martin was an established stage star (her Tony Award for The Sound of Music was her fourth) who had been, along with Rodgers and Hammerstein’s score, the best reviewed element of a production that was otherwise received tepidly by critics.

Meanwhile, Ethel Merman was an equally luminous star of the stage, and was appearing in a show that critics and audiences seemed to like quite well. Her role in Gypsy called on her dramatic abilities in a way her previous performances hadn’t—she traditionally relied more on her singular singing voice and comic abilities—and audiences and critics alike seemed to think she’d more than risen to the challenge. She had won one Tony Award in 1951 for her performance in Call Me Madam, but since then her performances had only earned her a single nomination, in 1957 for Happy Hunting. Many believed that if Ms. Merman were to win another Tony, it would be for this role.

But no matter what the critical response was to The Sound of Music, audiences were flocking to the show; it ran for nearly four years, while Gypsy ran for just under two. Fiorello! ended up running about two years, as well, but its subject matter (the life of beloved NYC mayor Fiorello H. LaGuardia) along with the well-received work of its writers Jerome Weidman, George Abbott, Jerry Bock and Sheldon Harnick, may have helped it win big on Tony night in 1960.

1976 – Chicago vs. A Chorus Line

In June of 1975, John Kander, Fred Ebb and Bob Fosse’s new musical Chicago opened on Broadway starring Chita Rivera and Gwen Verdon. Despite its popularity now (a Broadway revival opened in 1996 that is still running today, and a 2002 oscar-winning movie adaptation is credited by many with bringing back the genre of movie musicals), the original production was met with mixed critical reception.

The performances by Gwen Verdon, Chita Rivera and Jerry Orbach were highly praised along with Bob Fosse’s stylized direction and choreography, and audiences seemed happy enough with the show. It went on to run for over two years and nearly 1,000 performances. It’s a show that is now nearly synonymous with Broadway, a favorite for theatre fans around the world.

But two months after Chicago originally opened on Broadway, a little show called A Chorus Line opened at the Shubert Theatre. It had enjoyed a run just a few months earlier downtown at The Public Theater. The word of mouth leading up to the Off-Broadway engagement was so strong that the entire run sold out before it began performances, and a Broadway transfer became inevitable. Sound familiar?

Unfortunately for Chicago, there was no stopping the Chorus Line train even nine months later at the 1976 Tony Awards. Chorus Line won nine Tony Awards including Best Musical, and Chicago walked away with none.

1982 – Dreamgirls vs. Nine

Both Dreamgirls and Nine featured books and scores by writers new to the world of Broadway musicals. Dreamgirls was written by Henry Krieger, who was making his Broadway debut, and Tom Eyen, who at that time had only one previous Broadway outing—Rachel Lily Rosenbloom and Don’t You Ever Forget It—which closed during previews. Nine was written by Arthur Kopit, who had been a Pulitzer finalist and Tony nominee for his plays Indians and Wings but had never worked on a musical, and Maury Yeston, who was making his Broadway debut.

They were also both helmed by legendary and Tony-winning director/choreographers: Dreamgirls by Michael Bennett (Company, Follies, A Chorus Line, Ballroom) and Nine by Tommy Tune (The Best Little Whorehouse in Texas, A Day in Hollywood / A Night in the Ukraine, Cloud Nine).

Raising the stakes was the fact that Tune had been the protégé of Bennett; Tune appeared as a performer in the Bennett-choreographed A Joyful Noise in 1966 and Seesaw in 1973. Bennett saw a talent in Tune that went beyond performing and made him his associate choreographer on Seesaw as well, launching a career that saw Tune helming Broadway shows on his own just five years later.

As it turned out, Dreamgirls won six Tonys to Nine’s five, but it was Nine that took home the coveted Best Musical award. Tune also beat out his mentor, winning a Tony for his direction, while Bennett won for choreography along with Dreamgirls co-choreographer Michael Peters. Both shows have gone on to be revived on Broadway and adapted into movie musicals.

1984 – La Cage aux Folles vs. Sunday in the Park with George

By 1984, the landscape on Broadway had changed dramatically since the Golden Age of Rodgers and Hammerstein. Beginning with Company in 1970, Stephen Sondheim had, along with his collaborators, re-defined what a Broadway musical could be with a string of artistic and Tony-winning successes throughout the decade including Follies, A Little Night Music, Pacific Overtures and Sweeney Todd. His scores were written in a voice that was distinctly and uniquely Sondheim, and for the most part he seemed unconcerned with writing scores with pop sensibility.

Jerry Herman, on the other hand, had carried the torch of a more classic style of songwriting; his scores for Hello, Dolly! and Mame particularly are chock-full of Broadway classics. With La Cage aux Folles, however, he had lent his classic Broadway songwriting style to a show that was shocking and new to Broadway in terms of plot content as it tells the story of a gay male couple in 1970s France whose son is marrying the daughter of an ultraconservative and homophobic politician.

So palpable was the tension between the two writing styles on Tony night 1984 that Jerry Herman, while accepting his Tony for Best Original Score, said, “This award forever shatters a myth about the musical theatre. There’s been a rumor around for a couple of years that the simple, hummable show tune was no longer welcome on Broadway. Well, it’s alive and well at the Palace [La Cage’s original Broadway home].” Though he refrained from naming names, this was clearly aimed at no other than fellow Best Original Score nominee Stephen Sondheim, who has often spoke of being criticized for writing un-hummable songs.

When all was said and done, La Cage took home the lion’s share of Tony awards that night, including Best Musical. Sunday won Tonys only for its scenic and lighting designs, but won an excellent consolation prize a year later when it was awarded the 1985 Pulitzer Prize for Drama, the first musical to receive the award since A Chorus Line in 1976. Both musicals remain well-loved and often-produced today.

1988 – The Phantom of the Opera versus Into the Woods

The contest between Phantom and Into the Woods again pitted Stephen Sondheim against a dramatically different musical ideology, but this time there were even more layers to the race. Helming Phantom was director Hal Prince, who directed and produced most of Sondheim’s musicals through Merrily We Roll Along in 1981; he was just as responsible for the artistic growth in the form of the American musical as Sondheim was.

Prince had also worked his magic on Andrew Lloyd Webber’s Evita in 1978, so The Phantom of the Opera was a reunion for the two. Part of a series of big-budget and highly-successful West End transfers from the late ’80s and ’90s (that also included Evita, Cats, Les Misérables and Miss Saigon) The Phantom of the Opera was opulently produced with elaborate sets, costumes and special effects. It was much anticipated in 1988 and a hot ticket once it arrived.

Into the Woods, on the other hand, was thought of as one of Sondheim’s more accessible works. Though it had a dark second act, the hilarious book and score and fairy tale plot made the show more successful with audiences than his works generally had been.

When Tony nominations were announced in 1988, Into the Woods and The Phantom of the Opera predictably led the musical categories; they both received ten. Surprising no one, Phantom took home all of the musical design awards. Hal Prince beat out James Lapine, Woods’ director and book writer, to win the best direction award, but then Woods won awards for Best Score, Best Book and Best Leading Actress (Joanna Gleason, for her performance as The Baker’s Wife). Having separately swept the writing and design awards, it was anyone’s guess which show would take home Best Musical, but it was Phantom who walked away with the prize.

Today both shows remain beloved and popular. Into the Woods is regularly one of the most-produced musicals at high schools, community theatres and regional theatres around the world, and it received a successful screen adaptation in 2014. The Phantom of the Opera, on the other hand, is still there at the Majestic where it’s been since opening in 1988. As of early June, it has played for 11,798 Broadway performances, the longest-running Broadway show in history.

1998 – Ragtime vs. The Lion King

Broadway received two mega musicals in the 1997-1998 season, and whereas lavishly produced musicals often get a bad rap for lacking substance, Ragtime and The Lion King alike seemed to bring both art and commerce.

The Lion King, Disney’s second Broadway outing after their wildly successful production of Beauty and the Beast, opened at the New Amsterdam Theatre November 1997, helmed by director and puppet designer Julie Taymor. Tasked with depicting a cast of characters all of whom are animals, Taymor devised a visually stunning production that featured elaborate African-influenced masks and puppets. Audiences and critics were charmed, and the show immediately became a huge hit. It’s still playing on Broadway today, at the Minskoff theatre.

Ragtime opened a few months later, in January 1998, across the street at the newly-opened Ford Center for the Performing Arts (now the Lyric, home to Paramour). Critics seemed less enthused (Ben Brantley writing in the New York Times said “there [was] finally little to fall in love with.”), but the theatre community seemed to find lots to admire about it; the production received 13 Tony Award nominations to Lion King’s 11.

When the Tonys were handed out on June 7, Ragtime did pretty well; it won Tonys for Best Orchestrations, Score, Book and Featured Actress, but it was The Lion King that won Best Musical, direction and all of the design awards.

Ragtime has nevertheless continued to be a favorite amongst theatre fans. It was revived on Broadway in 2009 following a production that played the Kennedy Center in Washington, DC, and Manhattan Concert Productions presented a concert staging of the piece at Lincoln Center’s Avery Fisher Hall in February 2013.

2003 – Wicked vs. Avenue Q

Despite receiving some negative reviews, Wicked opened on Broadway in October 2003 an almost instantaneous success. The subject matter, the backstory to the Wicked Witch of the West from L. Frank Baum’s The Wizard of Oz, connected with audiences, as did Stephen Schwartz’s dynamic score. It also helped that leading the original cast were Idina Menzel, then known for her performance in Rent, and Kristin Chenoweth, a Tony winner for her performance in the Broadway revival of You’re a Good Man, Charlie Brown. Both were ideally suited to their roles as Elphaba and Glinda, respectively, and the show catapulted both to success outside the realm of Broadway soon thereafter.

Wicked’s composer, Stephen Schwartz, was no stranger to Broadway; his earlier scores include Godspell, Pippin, The Magic Show, The Baker’s Wife, Working and Rags. He was nominated for all of those Broadway efforts, but actually winning a Tony had proved elusive. Wicked was a big fat Broadway hit, and many thought this would be his year to win.

Enter the little show that could, Avenue Q. This hilarious adult spin on Sesame Street had opened Off-Broadway in March 2003, but made the jump to Broadway the following summer. It was a bonafide hit with critics and audiences alike, but it was still nowhere near the juggernaut that Wicked was, and by design.

There was no surprise that the two were nominated against each other for best musical at the 2004 Tony Awards, but the early consensus seemed to be that Wicked had it clinched; leading up to the Tonys, it won best musical Drama Desk, Drama League and Outer Critics Circle awards.

But Avenue Q launched an unprecedented Tony campaign, distributing a special song written by the shows authors Robert Lopez and Jeff Marx, “Vote Your Heart.” The message was clear: Voting your heart meant casting your vote for Avenue Q.

The campaign worked. Avenue Q won Best Musical in addition to Best Score and Book. Luckily for Wicked, it turned out they didn’t need the best musical Tony; the production is still playing to sell-out crowds regularly and it has spawned wildly successful international productions all over the world. Avenue Q is still running too, though it transferred back to Off-Broadway in 2009.

Logan Culwell is a musical theatre historian, Playbill's manager of research and curator of Playbill Vault. Please visit LoganCulwell.com.