Christopher Cross remains one of the most celebrated voices in soft rock history, delivering smooth melodies and sophisticated arrangements that defined adult contemporary music in the 1980s. His self-titled debut album achieved unprecedented success, making him the first artist in Grammy history to win all four general field awards in a single ceremony Wikipedia. From chart-topping ballads to hidden gems spanning four decades, these twenty songs showcase the artistic brilliance of this yacht rock pioneer.
Sailing
“Sailing” stands as arguably the greatest yacht rock song ever created, earning Cross three Grammy Awards including Song of the Year and Record of the Year Smooth Radio. The track’s inspiration came from Cross’s teenage friendship with Al Glasscock, who would take him sailing during high school years in San Antonio, Texas. Cross reunited with Al in 1995 after 28 years and sent him a copy of the platinum LP for selling more than five million copies of “Sailing” Smooth Radio. The song’s gentle acoustic guitar work and Cross’s silky vocals create an escapist fantasy that perfectly captures the freedom of being on open water.
Arthur’s Theme (Best That You Can Do)
This collaboration with pop legend Burt Bacharach and Carole Bayer Sager served as the main theme for the 1981 film “Arthur” starring Dudley Moore and Liza Minnelli Smooth Radio. The song achieved remarkable success, winning the Oscar for Best Original Song and reaching number one on the Billboard Hot 100 for three weeks. The track became Cross’s second and last American number-one hit, demonstrating his ability to craft memorable melodies with sophisticated lyrical content Wikipedia. Its optimistic message about seizing life’s opportunities resonated with audiences worldwide.
Ride Like the Wind
Featuring backing vocals by Michael McDonald, “Ride Like the Wind” hit number two on the U.S. Hot 100 and became a defining track from Cross’s Grammy-winning debut album Wikipedia. The song tells the compelling story of a man fleeing across the Mexican border, driven by urgency and desperation. Cross’s narrative approach combined with the track’s driving rhythm section creates an atmosphere of tension and movement that set it apart from typical soft rock ballads. The guitar work showcases Cross’s underrated skills as a musician, while McDonald’s harmonies add depth to the urgent vocal delivery.
Think of Laura
This heartfelt ballad reached number nine on the charts and became Cross’s final top 10 hit in the United States Smooth Radio. Cross wrote the song to mourn the death of Denison University student Laura Carter, who was killed when struck by a stray bullet during gang-related gunfire in Ohio Smooth Radio. The track served as comfort for Cross’s girlfriend Paige McNinch, Carter’s college roommate, and became a tribute to Carter’s memory. The song’s emotional weight and beautiful arrangement later found new life when it was used on the daytime soap opera General Hospital.
All Right
“All Right” served as the lead single from Cross’s second album “Another Page,” giving him another Top 15 hit in the United States ClassicRockHistory.com. The track features both Michael McDonald and several Toto members, creating a supergroup collaboration that enhanced the song’s appeal Smooth Radio. CBS Sports used “All Right” for its highlights montage following the 1983 NCAA Division I men’s basketball tournament Wikipedia. The song’s upbeat tempo and positive message made it a perfect soundtrack for celebratory moments.
Never Be the Same
“Never Be the Same” went number one on the Adult Contemporary chart and became another Top 20 hit from Cross’s debut album Wikipedia. The song explores themes of transformation and personal growth through love, delivered with Cross’s signature smooth vocal style. Its sophisticated arrangement includes subtle jazz influences that would become a hallmark of Cross’s sound. The track demonstrates his ability to craft introspective lyrics while maintaining commercial appeal.
Say You’ll Be Mine
Featuring backing vocals by Nicolette Larson, “Say You’ll Be Mine” rounded out the impressive collection of hits from Cross’s self-titled debut album Wikipedia. The song showcases Cross’s romantic side with tender lyrics about commitment and devotion. Larson’s harmonies complement Cross’s lead vocals perfectly, creating a warm and inviting sonic landscape. The track’s gentle acoustic foundation and subtle orchestration exemplify the sophisticated production values that made Cross’s debut album so successful.
Swept Away
This gorgeous ballad from the “Back of My Mind” album sounds even better when Cross performs it as an acoustic track Smooth Radio. The song was featured in the TV show “Growing Pains” during a video montage while Kirk Cameron’s character fell in love with a local girl during a family vacation in Hawaii Wikipedia. The track’s dreamy quality and emotional depth showcase Cross’s mature songwriting abilities. Its placement in popular television helped introduce Cross’s music to a new generation of listeners.
I Really Don’t Know Anymore
This track represents the second song on Cross’s self-titled debut album, which won him the Grammy for Album of the Year in 1981, beating Pink Floyd’s “The Wall” Smooth Radio. The song explores themes of uncertainty and self-doubt with remarkable honesty and vulnerability. Cross’s introspective lyrics combined with his smooth vocal delivery create an intimate listening experience. The track demonstrates his ability to address complex emotional topics while maintaining the sophisticated sound that defined his early career.
Minstrel Gigolo
Featured on Cross’s debut album, this track contributed to what critics note as one of the greatest soft rock albums of all time and a definitive yacht rock recording Smooth Radio. The song showcases Cross’s storytelling abilities through character-driven lyrics and theatrical elements. Its unique subject matter and musical arrangement set it apart from conventional love songs of the era. The track highlights Cross’s willingness to explore unconventional themes while maintaining his signature musical style.
Charm the Snake
“Charm the Snake” was the sole success from Cross’s album “Every Turn of the World,” reaching No. 68 in the Billboard Hot 100 Wikipedia. This unique ballad with tempo tells the story of a racecar driver, an original theme rarely explored in popular music ClassicRockHistory.com. The song could also be interpreted as a metaphor for relationships, demonstrating Cross’s ability to work on multiple lyrical levels. Its driving rhythm and compelling narrative showcase Cross’s continued evolution as a songwriter.
Loving Strangers
This track from Cross’s later catalog showcases his mature approach to relationships and human connection. The song explores the paradox of feeling isolated even when surrounded by people who care about you. Cross’s vocal performance conveys both longing and resignation, while the musical arrangement maintains the sophisticated production values that define his work. The track demonstrates his continued relevance as a songwriter even as musical trends shifted around him.
Words of Wisdom
Featured on Cross’s “Another Page” album, this track reveals his philosophical side through thoughtful lyrics about life experience and personal growth. The song’s gentle acoustic foundation supports Cross’s reflective vocals as he shares hard-earned insights about love and loss. The arrangement includes subtle string sections that enhance the track’s contemplative mood. This deep cut shows Cross’s ability to create meaningful album tracks beyond his hit singles.
No Time for Talk
“No Time for Talk” appeared as one of the singles from “Another Page” alongside the more successful “All Right” and “Think of Laura” Wikipedia. The song addresses communication breakdown in relationships with Cross’s characteristic sensitivity and musical sophistication. Its mid-tempo groove and layered harmonies create an engaging listening experience. The track demonstrates Cross’s consistent quality across album cuts, not just his better-known hits.
Poor Shirley
This track appears on Cross’s October 2024 release, showing his continued creative output in recent years Christopher Cross. The song tells a compassionate story about a character facing life’s challenges, delivered with the empathy that has always characterized Cross’s best work. His vocals retain the smooth quality that made him famous while conveying emotional maturity gained through decades of experience. The track proves that Cross’s songwriting abilities remain sharp well into the 2020s.
The Light Is On
Featured on Cross’s 2024 album release, “The Light Is On” represents his recent musical direction Christopher Cross. The song offers hope and guidance through metaphorical imagery about finding your way home. Cross’s production maintains the sophisticated approach that defined his classic work while incorporating contemporary elements. The track shows his ability to adapt his sound for modern audiences without sacrificing his distinctive musical identity.
Spinning
Another track from Cross’s October 2024 album, “Spinning” explores themes of confusion and disorientation in modern life Christopher Cross. The song’s title reflects both literal and metaphorical meanings as Cross examines feeling lost in an increasingly complex world. His mature vocal approach brings gravity to lyrics that might seem simple on the surface. The track demonstrates his continued ability to find fresh perspectives on universal human experiences.
Feel Flows
Released as a single in 2021, “Feel Flows” represents Cross’s recent collaborative work and continued recording activity Apple Music. The song showcases his ability to work with contemporary production techniques while maintaining his signature sound. Cross’s vocals blend seamlessly with modern arrangements that respect his classic aesthetic. The track proves his relevance to current headphones and streaming audiences discovering his music.
Freedonia
With his band Freedonia, Cross released the self-titled album in 2018, showing his continued creative collaboration with Austin musicians Wikipedia. The track represents Cross’s exploration of group dynamics after decades as a solo artist. His vocals blend with other band members to create a different texture than his solo work. The song demonstrates his willingness to experiment with new musical approaches while drawing on his extensive experience.
Firefly
From Freedonia’s second album “Firefly” released in 2019, this track continues Cross’s collaborative period with Austin-based musicians Wikipedia. The song explores themes of fleeting beauty and temporary connections through the metaphor of fireflies. Cross’s contributions to the band setting show his generous spirit as a collaborator rather than dominating frontman. The track proves his continued passion for making music regardless of commercial expectations.
Christopher Cross’s musical legacy spans from Grammy-sweeping hits to recent collaborative efforts, proving his enduring relevance in popular music. His sophisticated approach to melody and harmony influenced countless artists in the soft rock and yacht rock genres. Cross continues touring actively, including his 2025 collaboration with Toto on the Dogz of Oz tour across the U.K. and Europe Wikipedia. Whether exploring personal themes through music recommendations or crafting perfect summer anthems, Cross remains a master of his craft. These twenty songs represent the breadth of an artist who transformed smooth vocals and thoughtful songwriting into timeless musical moments.
Frequently Asked Questions
What is Christopher Cross’s biggest hit song?
“Sailing” stands as Christopher Cross’s biggest hit, reaching number one on the Billboard Hot 100 and earning him three Grammy Awards including Song of the Year and Record of the Year. The track defined yacht rock as a genre and sold over five million copies, making it one of the best-selling soft rock songs of all time.
How many Grammy Awards did Christopher Cross win?
Christopher Cross won five Grammy Awards for his debut album and became the first artist in Grammy history to win all four general field awards in a single ceremony. He took home Record of the Year, Album of the Year, Song of the Year, and Best New Artist at the 23rd Annual Grammy Awards in 1981.
What movies featured Christopher Cross songs?
“Arthur’s Theme (Best That You Can Do)” served as the main theme for the 1981 film “Arthur” starring Dudley Moore and Liza Minnelli, winning the Oscar for Best Original Song. “Ride Like the Wind” was also featured on the “Anchorman 2: The Legend Continues” soundtrack in 2013.
Is Christopher Cross still making music in 2024?
Yes, Christopher Cross released a new album in October 2024 featuring tracks like “Poor Shirley,” “The Light Is On,” and “Spinning.” He also continues touring and joined Toto as a special guest on their 2025 Dogz of Oz tour across the U.K. and Europe.
What band did Christopher Cross form in Austin?
In 2018, Christopher Cross joined with other Austin musicians to form the band Freedonia. They have released two full-length albums: “Freedonia” (2018) and “Firefly” (2019), plus an EP titled “Bring Back The Dinosaurs” (2021).