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A Certain Smile, A Certain Sadness is an album by Astrud Gilberto and Walter Wanderley, recorded in September 1966.

It was released by Verve Records at the height of the Bossa Nova craze in the United States, and featured the two most popular Bossa Nova musicians at the time: vocalist Astrud Gilberto and organist Walter Wanderley. A 1998 CD reissue added two songs recorded during the same sessions that yielded the album (https://en.wikipedia.org/wiki/A_Certain_Smile,_a_Certain_Sadness).

AllMusic Review by Christian Genzel:
In 1966, the bossa nova craze was at a peak, and A Certain Smile, A Certain Sadness marked a collaboration between two of its biggest stars — vocalist Astrud Gilberto, brought to fame by her classic rendition of “The Girl from Ipanema,” and organist Walter Wanderley. Even though the album is good, it is not as exciting as one might hope. While the music is remarkably innocent and sweet, with just a little underlying touch of sadness beneath the joyous, even naïve, surface, Gilberto and Wanderley do not always seem to work together on these tracks — it often appears as if each is performing in a universe of his or her own. That being said, there are many bright sides to the album, too: Wanderley’s organ playing is as enthusiastic and fluffy as ever, while Gilberto’s singing (in both English and Portuguese) remains smile-inducing. Both manage to create an incredibly warm sound, and when Wanderley plays some piano (as on the beautiful “A Certain Sadness”), you can sense a spark between the two. So, while A Certain Smile, A Certain Sadness might not be the most successful album of all time, it is still a nice record that fans of either Gilberto or Wanderley will want to have. And – even though one tends to use the word “cocktail lounge music” – their rendition of “Tristeza” is simply irresistible, easy listening or not.

Track listing:
1. “A Certain Smile” Sammy Fain, Paul Webster 1:27
2. “A Certain Sadness” Carlos Eduardo Lyra, John Court 3:08
3. “Nega do Cabelo Duro” Reubens Soares, David Nasser 2:18
4. “So Nice (Summer Samba)” Marcos Valle, Paulo Valle, Norman Gimbel 2:41
5. “Você Já Foi à Bahia” Dorival Caymmi 2:15
6. “Portuguese Washerwoman” André Popp, Roger Antoine Lucchesi 1:30
7. “Goodbye Sadness (Tristeza)” Edu Lobo, Niltinho, Norman Gimbel 3:33
8. “Call Me” Tony Hatch 3:20
9. “Here’s That Rainy Day” Jimmy Van Heusen, Johnny Burke 2:43
10. “Tu Mi Delirio” César Portillo de la Luz 3:38
11. “It’s a Lovely Day Today” Irving Berlin 2:39

Personnel:
Astrud Gilberto – vocals
Walter Wanderley – organ
José Marino – bass
Claudio Slon – drums
Bobby Rosengarden – percussion
Also, João Gilberto may have played guitar on tracks 2, 7, and 13

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Released: 1967
Recorded: September 20-23, 1966, NYC
Length: 29:47
Label: Verve
Producer: Creed Taylor