Bing Sings Whilst Bregman Swings (1956)
If you want to hear Crosby completely unleashed, this is your record. At a time when Frank Sinatra was dominating the charts with swaggering concept albums, arranger Buddy Bregman convinced Bing to do the same. The result is a high-energy, brass-heavy
affair that pushes Crosby out of his relaxed comfort zone. Some critics at the time found the arrangements almost too powerful, but listened to today, it’s a thrilling showcase of his impeccable timing and ability to ride a powerful big band beat. He tackles standards he’d never recorded before, and the sheer joy of the performance is infectious. It’s Crosby, the confident jazz singer, in full flight.
High Society (1956)
More than just a movie soundtrack, this album is a historic summit of musical giants. Crosby shares the microphone with Frank Sinatra, Celeste Holm, and the one-and-only Louis Armstrong. The Cole Porter songbook provides the ammunition, and the results are legendary. Highlights include the playful duet 'Well, Did You Evah!' with Sinatra and the iconic 'Now You Has Jazz' with Armstrong, which serves as a perfect lesson in the genre’s history. The album also features Crosby’s stunning performance of 'True Love' with Grace Kelly, a song that became a massive hit and a cultural touchstone. It’s a perfect snapshot of mid-century cool.
Songs I Wish I Had Sung the First Time Around (1956)
The concept is simple and brilliant: Bing Crosby takes on the signature songs of his contemporaries. It’s a gesture of respect and a masterclass in interpretation. He tips his hat to Al Jolson ('April Showers'), Nat King Cole ('Mona Lisa'), and even his friend Bob Hope ('Thanks for the Memory'). Rather than trying to outdo the originals, Crosby inhabits each song with his signature warmth and effortless charm, making them his own. The album stands as a testament to his confidence and his deep appreciation for the great American songbook, proving he could find the heart of any tune, no matter who sang it first.
Bing & Satchmo (1960)
Two of the most influential voices of the 20th century finally got together for a full album, and the result is pure, unadulterated joy. Crosby had long cited Louis 'Satchmo' Armstrong as a primary influence, and Armstrong deeply respected Crosby's golden tone. That mutual admiration shines through on every track. Arranged by the great Billy May, the album is a playful, New Orleans-flavored party from start to finish. From 'Muskrat Ramble' to 'Way Down Yonder in New Orleans', their voices weave together with an easy, almost telepathic chemistry. It’s not a formal, serious record; it’s the sound of two masters having a blast.
El Señor Bing (1960)
Just when you think you have him pegged, Crosby takes a delightful detour south of the border. This Latin-themed album is a wonderful surprise in his discography, showing his willingness to explore different rhythms and moods. Backed by Billy May's orchestra once again, Bing tackles a collection of Spanish and Latin American-inspired songs. While it might seem like a novelty project, Crosby’s performance is committed and full of his characteristic charm. The arrangements are lush and atmospheric, making for a fun and breezy listen that showcases a different, more adventurous side of the crooner.
Seasons (1977)
Released shortly after his death, 'Seasons' is Crosby's final studio album and a profoundly moving farewell. The record is a concept album, with each song themed around a different time of year, from 'June in January' to 'Autumn in New York'. But it also serves as a poignant metaphor for the seasons of a life. His voice, though older, is filled with warmth, wisdom, and a touch of melancholy, especially on the standout track 'Yesterday When I Was Young'. Marketed as 'The Closing Chapter', it’s an elegant and reflective end to an unparalleled career, proving his artistry remained potent until the very end.
