The 1940s and 1950s were a golden era for Broadway, a time when the Best Musical Tony Award recognized some of the most iconic shows ever staged. But not all winners are created equal. In this weekend’s Saturday List, we’re ranking all the Best Musical Tony Award winners from these two decades, from the most forgettable to the truly timeless, taking into account their cultural impact, musical innovation and audience reception over time.
11. Kismet (1954)
A musical with a grand setting and an ambitious score, Kismet is unfortunately as dated as they come. Drawing on the music of Russian composer Alexander Borodin and based on Edward Knoblock’s 1911 play of the same name, the show was adapted by Charles Lederer, Luther Davis, Robert Wright and George Forrest into a Middle Eastern fantasy that feels more like a relic than a classic. Set in ancient Baghdad, a wily poet (known as Hajj thanks to a case of mistaken identity) talks his way in and out of a series of escapades, while his daughter, Marsinah, becomes the object of the Caliph’s affection. The show’s portrayal of what some might describe as exotic is uncomfortable by today’s standards, making it hard for modern audiences to connect with the material, despite a trio of songs that have become standards, “Baubles, Bangles and Beads,” “Stranger in Paradise” and Änd This is My Beloved.” A complete reimagining would be needed to breathe new life into this one.
10. Redhead (1959)
Redhead is a show that, despite its Tony win, feels like it barely left a mark. Set in Edwardian London, the musical revolves around Essie Whimple, a young woman embroiled in a murder mystery – a plot that sounds like it should be more engaging than it is. Without diving into spoiler territory, book-writers Dorothy Fields, Herbert Fields, Sidney Sheldon and David Shaw provide all the requisite twists and turns – but the show never truly hits the mark in its overall tone. The score by Albert Hague and Dorothy Fields is serviceable but lacks the spark to make it truly memorable. Without Gwen Verdon and Bob Fosse’s star power, this one might have faded into obscurity altogether. It’s a show of its time, but not one for the ages. (We’ve looked at Redhead in a bit more depth in our Forgotten Musicals Friday series, so if you’re keen to find out more about the show, then look no further.)
9. The Music Man (1957)
Meredith Willson’s The Music Man is a quintessential piece of Americana, brimming with charm and optimism. The story of Harold Hill, a con man who turns a small Iowa town upside down, and Marian Paroo, the local liberation with whom he falls in love and who sees right through him, is full of heart and humour. However, its strong ties to a specific time and place in American culture often leave international audiences feeling somewhat distanced from the way it says what it has to say. While songs like the ebullient “Seventy-Six Trombones” and its sweet counterpart, “Goodnight, My Someone,” as well as the groundbreaking “(Ya Got) Trouble” and the breakaway hit “Till There Was You” are undeniably catchy, the show’s cultural specificity keeps it from placing higher on this list.
8. The Pajama Game (1954)
The Pajama Game is a delightful romp through labour disputes and romance at the Sleep-Tite Pajama Factory, where the new superintendent, Sid Sorokin, and Katherine “Babe” Williams, the leader of the factory workers’ Union Grievance Committee, fall in love from opposite sides of the picket line. The music and lyrics by Richard Adler and Jerry Ross provide plenty of memorable moments, from the plaintive “Hey There” to the sultry “Steam Heat.” Yet, while the show is thoroughly enjoyable, it doesn’t quite hit the heights of some of its contemporaries. Adler and Ross had a brief but brilliant partnership, and this show hints at what might have been had they had more time to develop their craft beyond their second big Broadway success, which is next up on the list.
7. Damn Yankees (1955)
Baseball, Faustian bargains, and musical comedy might seem like a strange mix, but Damn Yankees pulls it off with style. The show tells the story of middle-aged Joe Boyd, who sells his soul to become the young star slugger of the Washington Senators, someone who can lead his team to victory. Richard Adler and Jerry Ross struck gold with songs like “Heart,” “Whatever Lola Wants,” and “A Little Brains, A Little Talent” and “Those Were the Good Old Days.” While some of the dramatisation is a little basic, the characters and the music elevate it to a level that transcends its all-American roots.
6. Wonderful Town (1953)
Set in the bohemian quarters of 1930s New York, Wonderful Town follows Ruth and Eileen, two sisters from Ohio, as they try to make it big in the big city. Leonard Bernstein’s vibrant music, combined with Betty Comden and Adolph Green’s witty lyrics, captures the hustle and bustle of city life with infectious energy; the score yielded several classic songs like “Ohio,” “One Hundred Easy Ways,” “A Little Bit in Love” and “Conga.” The show stands out for its sophistication, offering a sharp, comedic take on the classic “small-town girls in the big city” narrative. It’s a gem that has aged remarkably well, its source material having been adapted in many different ways – on stage, for the radio, on film and on television.
5. Kiss Me, Kate (1948)
A backstage musical comedy inspired by Shakespeare’s The Taming of the Shrew, Kiss Me, Kate is a dazzling showcase for Cole Porter’s talents as one of the great songwriters of his time. The score is packed with hits like “So in Love” and “Too Darn Hot,” and the show-within-a-show structure provides plenty of opportunities for theatrical fun as the real-life bickering between the stars, Fred Graham and Lilli Vanessi, threatens to upstage the production. Despite some narrative oddities – like the mysterious writers working behind the scenes that the audience never gets to see and the gangsters who suddenly become performers in the classic “Brush Up Your Shakespeare” number – the sheer entertainment value of Kiss Me, Kate makes it a perennial favourite. (The film adaptation, while by no means perfect, managed to smooth out both of those rough spots.)
4. The King and I (1951)
Richard Rodgers and Oscar Hammerstein II’s The King and I is a grand, sweeping musical that grapples with cultural clashes and personal connections. Set in the royal court of Thailand, the story follows a British schoolteacher, Anna Leonowens, who challenges the traditions of Mongkut, King Rama IV of Siam, while forming a bond with him and his children. The score is lush and evocative, with songs like “Hello, Young Lovers” and “Shall We Dance?” standing out as highlights and sequences like “The Small House of Uncle Thomas” setting a benchmark for the time in theatrical innovation. Despite some problematic elements in its portrayal of Thai culture, partly because it blends together influences from all over Eastern Asia, the show remains a powerful exploration of change and understanding. Productions like Bartlett Sher’s revival show that, with careful direction, the show can still captivate modern audiences – but the fact that such great care has to be taken in staging this material in this day and age reveals something about the material itself.

3. My Fair Lady (1956)
My Fair Lady is often hailed as the perfect musical by the critics and its fans, and it is indeed a significant one, despite some less than meticulous lyrics from Alan Jay Lerner, who collaborated on the show with composer Frederick Loewe. Their adaptation of George Bernard Shaw’s Pygmalion is a triumph of style and substance, exploring themes of class, gender and transformation. The story of Eliza Doolittle’s metamorphosis from a Cockney flower girl to a refined lady is brought to life with a sparkling score that includes classics like “I Could Have Danced All Night” and “Wouldn’t It Be Loverly.” Even with its few missteps, My Fair Lady remains a landmark in musical theatre, adding to a theatrical conversation started by A Doll’s House many decades earlier and continuing with Top Girls a couple of decades later.
2. Guys and Dolls (1950)
Frank Loesser’s Guys and Dolls is musical comedy at its finest. Set in a world of gamblers, showgirls, and missionaries, the show weaves together multiple storylines with wit and charm. When Nathan Detroit bets fellow gambler Sky Masterson that he can’t get virtuous Sarah Brown to go on a date with him, unexpected romantic entanglements have to be unravelled – including Nathan’s own fourteen-year engagement to Miss Adelaide. The characters are unforgettable, from the adenoidal Miss Adelaide to the smooth-talking Sky. The score is packed with hits, including swinging “Luck Be a Lady,” the emotionally complex “I’ll Know” and the show-stopping “Sit Down, You’re Rockin’ the Boat,” making it a joyous celebration of the golden age of Broadway. Its blend of humour, romance, and irresistible tunes secures its place near the top of this list.
1. South Pacific (1949)
South Pacific is not just a musical; it’s a cultural touchstone. Rodgers and Hammerstein’s masterpiece tackles serious themes of racism and prejudice while delivering some of the most beautiful music ever written for the stage. The story, set against the backdrop of World War II, explores the love affair between an American nurse, Nellie Forbush, and a French plantation owner, Emile de Becque,
and the conflict that arises when she finds out that his deceased ex-wife, was Polynesian. The score includes unforgettable songs like the classic “Some Enchanted Evening,” the profoundly romantic “This Nearly Was Mine” and the socially significant “You’ve Got to Be Carefully Taught.” Its relevance, dealing with the kind of thing that happens when nobody talks about race or racism and just emulates the attitudes of the world they grew up in, has only grown over time, making South Pacific not just one of the best musicals of its era, but one of the greatest of all time.
Final Thoughts
The 1940s and 1950s were transformative decades for Broadway, a time when the Best Musical Tony Award celebrated shows that would come to define the American musical theatre canon. As we’ve seen, not every winner has aged gracefully, with some musicals struggling to find their place in the modern repertoire. However, those that have stood the test of time continue to captivate audiences with their memorable scores, compelling stories, and rich characters. Whether tackling profound social issues or offering lighthearted escapism, these musicals reflect the diversity and creativity that have made Broadway an enduring cultural force. Our ranking is subjective, of course, but it’s clear that even the most dated of these shows have played a significant role in shaping the history of musical theatre. As we look back on these iconic works, we can appreciate not only their individual achievements but also the broader legacy of an era when Broadway was at the height of its powers.























