There was recently an interesting episode of the podcast 99% invisible about the first Elvis Presley stamp, which was the first stamp featuring pop culture (at least in the US): You Ain't Nothin But a Postmark - 99% Invisible
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The one and only Thailand stamp issue with a singer was issued in 2010.
He is Mr. Euah Suntornsanan, the founder of “Suntaraporn” Band. He was a singer and composer with many Western-style Thai songs that they’ve been still unique until now.
In 2005, Hong Kong Post issued Hong Kong Pop Singers stamps issue with 5 legend deceased singers: Wong Ka Kui, Danny Chan, Roman Tam, Leslie Cheung and Anita Mui.
P. Ramlee, Malaysia famous actor, singer and filmmaker. He was famous from his movies and songs in Malaysia classic era. Pos Malaysia issued stamps to honor him in 1999.
PHLPost issued “Living Legends (series I)” stamps series with many famous “living” persons (and non-person for Jollibee mascot (the 3rd stamps on the last row)) was issued.
But the singer in this stamps issue is the 4th on the first row.
She is Lea Salonga. She has been famous from plays (Miss Saigon) and singing (especially many songs from Disney movie), e.g. A Whole New World from Aladdin, etc.
***PHLPost issued this series and “Living Legends” series II when the persons on the stamps were still alive. (Many countries aren’t issue stamps while each persons are still alive, except the Royal/Head of State or some Supreme Patrirach/Priests.)
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Regarding the “You Ain’t Nothin’” article, here’s a picture of the actual ballot by which people could vote for which Elvis stamp they wanted to see printed. The ballot was printed on a postcard that you could mail in. (Postage was required, of course).
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I had a look for singer-themed stamps from Portugal, and could only find a few…
These last ones are for bands, not singers. Maybe @bom_dia knows more?
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It isn’t really something within my scope of interest, but googling a bit, I found another series of Fado singers:
And some foreign singers, like this year’s issue of Maria Callas.
Oh, and of course, the issue dedicated to Cante Alentejano, Intangible Cultural Heritage from Unesco
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Used these two stamps for
(Yes, I know, the Beatles were not at Woodstock) 
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The most recent 
Chilean stamp that depict a singer is this one from 2017, dedicated to Violeta Parra:
Before that, we have to go back to 1998, when 2 stamps about Víctor Jara and Violeta Parra were issued:
Also, in 1997, 5 stamps about Chilean lyric singers were issued:
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I sent a letter with this stamp plus an old Händel stamp to the Händel-Hendrix house in London. They were thrilled to receive it!
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When I was in the UK, I noticed that the Royal Mail has issued quite a lot of singer/musician stamps. I tried to get the Rolling Stones stamp series but they weren’t available even in the large London post offices! Duh!
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It is 50 years since the fateful accident that took the life of that young man who sang about love and heartbreak.
Singer. Nino Bravo (1944-1973).
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In Belgium we have a stamp published in 1999 which comes from a block on the theme “20th century” with lots of famous people. Here it is the French singer Edith Piaf.
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Not too sure if it’s been mentioned yet, but Taiwan released a set of Fen Fei Fei (凤飞飞) stamps in 2022:
I managed to get a set of them when I visited Taiwan last year!
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Taiwan also released a set of stamps in memory of 鄧麗君 (Teresa Teng) in 2015.
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Here are some Canadian singers who have been featured on postage stamps over the years.
And Oscar Peterson (jazz pianist) didn’t usually sing, but I love him, so ~~
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Oh, I know Kishore Kumar. I even saw him as an actor in one old film (“Bombay to Goa”).
He often sang for Amitabh Bachchan.
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