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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.

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