Top 10 Hardest Barbra Streisand Songs to Sing

Bear in mind that Frédéric Chopin’s “Valse du petit chien” is nicknamed “minute” as in “small.” Of course, the brief waltz is no small feat on the piano. Lan O'Kun’s (Oaken) patter song interpretation is itself a challenge that few can meet like Barbra Streisand. In just over a minute, as in time, she playfully matches the piano’s uptempo rhythm and dynamic scales. As much breath as she carries through the wacky parody lyrics, she manages to punctuate most verses with stunning falsetto. Even the slow bridge has a classical grandeur. “The Minute Waltz” may essentially be as gimmicky as its wordplays suggest. But Streisand’s rendition is as sweetly whimsical as it is humorously hard.

It was 4 decades before fans got to hear “Lost in Wonderland” on a compilation album of Streisand outtakes. The psychedelic bossa nova may not readily fit the singer’s aesthetic, but she adapts with a literally breathtaking performance. The intervals are long, the key is low, and the pitch is precise. This beautifully conveys the enchantment and surrealism of a Lewis Carroll fairytale. The real challenge is in making the breezy ballad sound both viscerally intense and effortlessly charming. Whatever “Lost in Wonderland” may lack in the belting spectacle usually associated with Streisand’s virtuosity, it more than compensates in a masterpiece of dreamy breath control.

A 1958 spin on "Aladdin" is full of hidden gems by legendary songwriter Cole Porter. But the opening number was made timeless by Streisand's rendition on her debut album. She dramatically ups the tempo of the already wordy "Come to the Supermarket (in Old Peking)", turning it into an eager patter piece. Despite the excited frenzy, she still nails the bark and sweeping belts of a show tune showstopper. Let's be honest: "Come to the Supermarket" has gotten harder to sing because of its exotic stereotypes of Chinese culture. As catchy as Porter's lyric still is, Streisand's jumpy interpretation is all the more infectious to be all the more tricky.

Streisand's return to Broadway songs album opens with an obscure entry in the Stephen Sondheim songbook. "Putting It Together," from the musical "Sunday in the Park with George," is a fast-paced piece for multiple vocalists. Streisand performs all the singing parts solo, seamlessly blending multiple vocal styles and pitches in long, fast intervals. The range and concentration are incredible, but there's still a deliberate and growing frenzy. Sondheim himself rewrote the song to focus on the exhausting relationship between artists and the music industry. Still, Streisand perfectly captures the original lyric's expression of the difficulty in composing art. It's definitely more difficult to put together without the extra vocalists.

It's as if Streisand recognized her legacy in Celine Dion when they collaborated on the monumental "Tell Him." The verses display the virtuosos' distinct mastery of serene melody and longing, as they discuss and offer support for a situation of romantic uncertainty. The maturity and reassurance can be heard in their vocal interaction. Of course, the bridges and chorus explode with astonishingly soulful harmonies. The heart-wrenching and mind-blowing performance was nominated for a Grammy, and is now considered a highlight of Streisand and Dion's '90s catalogs. One singer capable of expressing that much passion is a gem. Never mind a pop duet you only get a few times in a generation.

Though the 1976 remake of “A Star Is Born” ends as tragically as all other versions, “Evergreen” ends the romance on a triumphant note. Streisand fills the escalating love ballad with both longing and nostalgia. By the climax, she’s soaring on hopeful high notes. It’s a quintessential Streisand anthem that hits particularly hard in swooning emotions and vocal range. Though the album version is an impressive solo, the duet with Kris Kristofferson in the film brings home the intensity through chemistry and vocal contrast. Lady Gaga may have put up stiff competition by closing 2018's “A Star Is Born” with “I’ll Never Love Again,” but the Golden Globe-, Oscar- and Grammy-winning “Evergreen” lives on as a daunting classic.

Barry Gibb was naturally key to Streisand perfecting her distinctive disco style on the album "Guilty." But she proved the perfect interpreter of his distinctive songwriting style with "Woman in Love." She nails the groovy swoon of a soft Bee Gees melody while incorporating her own bittersweet soul. It all infectiously blends for a chorus led by a hypnotic four-part harmony. This was the culmination of several refined vocal melodies forming something both ethereal and danceable. That's almost impossible to replicate. Sure, Streisand may be accused of playing a bit fast and loose with her acclaimed work with Gibb. But as one of her biggest hits, "Woman in Love" is also a unique vocal performance.

In addition to being a favorite romantic drama of the '70s, "The Way We Were" features one of the great heartbreak ballads as its theme song. Barbra Streisand's melancholy nostalgia piece may not sound like an exceptionally technical melody. Certainly, she makes it shine with her haunting swoons and escalating belts. But the key to this ballad is the depth of emotion that Streisand conveys like no other artist. Indeed, the real challenge in singing "The Way We Were" is not breaking into tears. The song, like the movie, was hailed as a masterpiece and pop culture phenomenon. It epitomizes how even a simple tune can sound mesmerizing with Streisand's voice.

Streisand’s musical passion project “Yentl” showcased her vocal range as much as her filmmaking ability. Some of the most soulful numbers of her career, as composed by the renowned Michel Legrand, all lead to the show-stopping “A Piece of Sky.” The epic crescendo is the culmination of the emotions felt by a woman trying to be heard. The heavy lows and soaring highs throughout the song are devastating enough. And then it all ends in a phenomenal high note that lasts 20 seconds. The aria is a fitting finale to “Yentl” and possibly the pinnacle of Streisand’s musical career. Streisand possesses a rare register, and “A Piece of Sky” plays it for all its worth.

Before we unveil our top pick, here are a few honorable mentions.

“Piano Practicing”, “Barbra Streisand… and Other Musical Instruments” (1973)
A Classical Vocal Warmup Still Can't Prepare You For the Patter with Paradisi's Piano

“I Never Has Seen Snow”, “Barbra Streisand… and Other Musical Instruments” (1973)
A Broadway Blowout's Rendition of a Harold Arlen Masterpiece

“Down with Love”, “The Second Barbra Streisand Album” (1963)
A Smoky Jazz Ballad Gradually Evolves Into a Swinging & Screaming Anthem

“I Can See It”, “My Name Is Barbra” (1965)
A Sweeping Crescendo from Soft Whimsy to an Explosive Final Belt

“The Main Event/Fight”, “The Main Event” (1979)
A Punchy Disco Medley with Strikingly High Hooks

The fiery "Don't Rain On My Parade" perfectly closes the first act of the Fanny Brice bio-musical "Funny Girl." And with the film adaptation, first-time film actress Barbra Streisand made the number a signature song. The triumphant rage against manipulation demands a fierce delivery at a hurried pace. Streisand keeps a theatrical bark throughout these vibrant verses, flawlessly punctuated by clean head voice refrains. These intense runs and playful melodic bridges build toward a massive finale, with a 12-second final note. This stunningly technical exercise became a sensation independent of "Funny Girl." "Don't Rain On My Parade" is now considered a major milestone in pop vocal performance. It may also be the definitive showcase of Babs' unparalleled singing skills.


What are your favorite Barbra Streisand songs to try singing along with? Get in tune in the comments.