Roberta Flack Quiz: Can You Name These Roberta Flack Classics?

Killing Me Softly with His Song became Roberta Flack’s iconic hit in 1973, topping charts and winning multiple Grammys. Years later, Lauryn Hill and The Fugees brought it back to global fame in the ’90s with a hip-hop twist. While Lauryn’s version is often better known among Gen Z, Roberta’s soulful interpretation laid the groundwork for the emotional pull the song carries. The answer is analytical in that it links musical legacy with cultural resurgence, showcasing how original hits transcend generations when revived by contemporary artists.

The First Time Ever I Saw Your Face catapulted Roberta Flack to fame after it was featured in Clint Eastwood’s 1971 film Play Misty for Me. Though originally written by Ewan MacColl, Roberta’s slow, heartfelt delivery turned the song into a massive hit, topping the Billboard charts and winning her a Grammy. It’s significant not only as her breakthrough but as an early 70s ballad that redefined slow-burning romance in soul music. Her careful timing and minimal instrumentation turned a simple love song into something hauntingly powerful.

Where Is the Love is one of the most celebrated Roberta Flack and Donny Hathaway duets. Released in 1972, it became an instant classic, winning a Grammy and symbolizing the peak of romantic R&B duets in that era. Its success lies in the lyrical simplicity, conversational phrasing, and perfect vocal harmony between the two artists. This song helped define the modern soul duet structure and remains a timeless example of musical chemistry. Its impact goes beyond genre—it’s used today to benchmark the sincerity and purity of vocal collaboration.

Jesse is a deeply personal and emotional track written by Janis Ian but made widely known through Roberta Flack’s rendition. The song touches on longing and vulnerability, themes Roberta interprets with subtlety and restraint. Her nuanced vocal delivery and piano-driven arrangement lend a quiet power that resonates with anyone who has experienced unspoken love or separation. The choice of this song reflects her mastery of storytelling—not just through lyrics but through vocal tone and timing. It shows how Roberta connects emotionally without over-performing the sentiment.

Feel Like Makin’ Love showcases Roberta Flack’s sensual vocal style merged with a jazz-inspired arrangement. It was written by Eugene McDaniels and reached No. 1 on the Billboard Hot 100 in 1974. This track stands out for its relaxed tempo and intimate production style, using layered instruments and breathy vocals to create a laid-back but emotionally rich experience. The song is often referenced for its influence on the quiet storm genre—a blend of soul, R&B, and jazz ideal for romantic listening. Roberta’s interpretation elevated it from flirtatious to timeless.

Trade Winds opens with a smooth, haunting piano line and dives into reflective lyrics that evoke images of escape, memory, and spiritual yearning. Unlike more commercial hits, this track demonstrates Roberta Flack’s artistry in using minimalist instrumentation to create mood and depth. The emotional tone of the song is rich with melancholic reflection, a signature of her balladry. Listeners are drawn in by the quiet storm ambiance—each note feels intentional. It’s a masterclass in holding back just enough to let the message breathe.

Compared to What stands out as one of the earliest examples of jazz-soul fusion with a strong political message. Originally recorded live at the Village Gate, Roberta’s version (often in collaboration with Les McCann and Eddie Harris) emphasizes themes like social injustice and war with biting lyrics. Its groove-heavy rhythm and charged tone made it a favorite during the civil rights era. The reason this is the correct answer lies in its historical context—it wasn’t just a song, it was protest in musical form, wrapped in funky, accessible instrumentation.

Jesse appears again here but in a new context—storytelling through melody. It’s a track where every word feels like a diary entry, delivered with restraint and fragility. This time the focus is on Roberta’s ability to turn a sparse composition into a narrative experience. She allows pauses and inflection to carry emotional weight, making listeners feel like they’re eavesdropping on a private thought. It’s more than a love song; it’s a window into grief, memory, and unspoken hope. The strength lies in its gentle clarity, not dramatic flair.

Killing Me Softly with His Song is not just a cover—it was originally inspired by Lori Lieberman’s poem and first recorded by her, but Flack’s 1973 version brought it mainstream success. Her subtle modulation and careful pacing make every verse feel like a personal confession. It became a No. 1 hit and earned multiple Grammy awards. It represents the gold standard for how a cover can outshine the original by emotional execution alone. Its staying power lies in its minimalist accompaniment and universal theme of feeling seen—and undone—by a song.

The Closer I Get to You was another hit duet with Donny Hathaway, released in 1978. Unlike “Where Is the Love,” this one is slower and more intimate, focusing on the growing emotional intensity between two people. It was a chart-topping success and became one of their most enduring collaborations. The vocal blend between Hathaway and Flack is flawless—there’s a call-and-response structure that mimics genuine conversation. Its appeal lies in how it balances romantic vulnerability with musical sophistication. This song set the template for emotional realism in soul duets.