Brazilian singer and composer Marcos Valle began making music in the early 60s, and since the 90s he’s been settled into a comfortable groove, apparently disinterested in developing his art or rocking the boat. He sticks to the same kind of slick, jazzy bossa nova that other musicians were already playing the late 70s; he makes the occasional album, most often for British label Far Out; and he tours, usually in Europe. The records he’s releasing now—the most recent is 2010’s Estatica—are pleasant enough, and he’s a talented musician who still writes strong melodies. But if Valle weren’t playing international jazz festivals and swanky clubs, he could easily make a living on Brazil’s nostalgia circuit.

In the early 70s, though, Valle seemed to be looking forward rather than back. He stretched as far from his roots in samba and bossa nova as he ever would, in the process making some of the best and most interesting records of his career. He collaborated with members of progressive Brazilian psych bands Som Imaginario and O Terço, among others, and injected his music with influences from rock, soul, folk, flamenco, gospel, and elsewhere. In February four of his albums from that period—1970’s Marcos Valle, 1971’s Garra, 1972’s Vento Sul, and 1973’s Previsao do Tempo—were released in the U.S. for the first time by Seattle imprint Light in the Attic.

Born in Rio de Janeiro in 1943, Valle emerged as a rising star of bossa nova in the mid-60s, just as the style was beginning to fall out of fashion in Brazil and catch on abroad. In 1965 he and Sergio Mendes toured the States, where Valle met Merv Griffin, who helped introduce him to the U.S. market. Valle spent 1966 in America, where just a couple years earlier bossa nova stars Antonio Carlos Jobim and Joao & Astrud Gilberto had found great success. That year Brazilian keyboardist Walter Wanderley scored a huge U.S. hit with an instrumental version of Valle’s “Samba de Verao” (better known by the English title “Summer Samba”). Valle signed with Warner Brothers, which in ’67 released an instrumental collection called Braziliance. The next year Valle worked with Verve to put out the lovely English-­language album Samba ’68, which included his own version of “Summer Samba.”

By the late 60s Brazil’s oppressive dictatorship made the sunny, carefree attitude of bossa nova seem out of step if not indulgent, but up till that point Valle and his lyricist brother, Paulo Sergio Valle, had refrained from writing populist or socially conscious bossas. The brothers were raised by a wealthy family and grew up on Rio’s beautiful beaches; they had trouble coming to grips with the ugly nationalism and widespread poverty that afflicted most of the country. But upon returning to Brazil, Valle began changing his music to reflect the tensions in his homeland. The same year he released the Americanized bossa of Samba ’68 in the States, he put out Viola Enluarada in Brazil; its bossas are darker and more pensive, and the title track features beautifully sorrowful lead vocals from rising star Milton Nascimento. From there his music became increasingly gloomy and baroque, though its foundation never ceased to be samba and bossa nova.

Light in the Attic includes present-day contributions from Valle in its new liner notes for his self-titled 1970 album, which on their face make it hard to understand the creative flowering he was undergoing. “I am not a very strong listener. There are some people that bring records and listen and listen to a lot of things to get some influences,” he says. “Or maybe not influences, but they are [consciously] aware of a lot of things that are happening. I’m not this kind of person. But, when I like something I really like to listen to it again.” Yet in an interview published by Wax Poetics in 2007, he acknowledges that he felt the influence of the tropicalistas during their late-60s heyday: “When those artists came along and mixed Brazilian music with guitars and pop, it felt new and good. I think it gave me the confidence to do what I had been thinking about for a while, to liberate myself in certain ways.”

Regardless of how actively Valle was listening to current music at the time, he was reaching out to musicians from different scenes to enrich his own work—this in spite of the fact that his deal with EMI in Brazil gave him access to studio musicians and an orchestra at the label’s Rio studio.

For that 1970 album, on whose cover Valle reclines shirtless in bed with a drink in one hand and a cigarette in the other, he worked with members of heavy psych-rock band Som Imaginario, including keyboardist Wagner Tiso, who’d later become a prominent jazz fusion player. Also on the record (but not a member of the band) was superb guitarist and arranger Nelson Angelo, who’d soon establish himself working with singer Joyce.

This isn’t to say Valle suddenly became a rocker—the instrumental “Ele e Ela,” whose opening horn part provided a sample for Jay-Z’s 2009 track “Thank You,” is a playful but somewhat shallow instrumental bossa, where he and his sister Angela pretend to be a kissy, giggly couple. But he was definitely experimenting with new sounds. “Dez Leis,” whose lyrics about the laws of God and the laws of man all but dared Brazil’s heavy-handed censors to intervene, borrows heavily from American soul for its gospelized piano licks and Valle’s raspy singing, while wonderfully fuzzed-out electric guitar leads embroider the breezy samba “Os Grillos.” The album closes with an ambitious four-part instrumental suite that collides pychedelic flourishes (dissonant piano, ticking clocks, wordless female singing, detuned guitar, harmonically odd horns) in a dissociative series of episodes—one of which accompanies a melancholy melody that reminds me of the Mamas & the Papas with a stiff backbeat and an electric harpsichord.

For 1971’s Garra, Valle relied entirely on his label’s house musicians, among them pianist Dom Salvador and orchestrators Geraldo Vespar and Cesar Camargo Mariano. A collection of breezy bossas, it pushed the envelope mainly with his brother’s censorship-skirting political lyrics. Though it includes buoyant ditties such “Com Mais de 30” and the title track, they rub elbows with “Black Is Beautiful,” an homage to America’s Black Power movement that became a big song for Elis Regina that same year, and the feel-good hippie love fest “O Cafona.”

Valle recruited outside help again for Vento Sul in 1972—psych-prog band O Terço helped push him as far afield as he ever went. The vocal harmonies on “Vôo Cego” recall Crosby, Stills & Nash, while electric guitarist Claudio Guimaraes contributes probing psychedelic leads. (He’s not a member of O Terço, but he did write the song.) “Democustico” was originally meant to be an instrumental, with a dancing groove, wandering flute, and insistent harpsichord, but Valle added a trippy recitation where he sticks the prefix “demo-” onto all sorts of words (whether the combination means anything in Portuguese or not). “Mi Hermoza” begins as a drifty, flamenco-tinged meditation with gorgeous falsetto singing, then breaks into a ferocious, crunching hard-rock riff that vanishes just as suddenly as it appeared.

For the last of the Light in the Attic reissues, 1973’s Previsão do Tempo, Valle brought in members of up-and-coming samba-jazz-fusion band Azymuth; rhythmically and structurally the music recalls his carefree past, except with more funky, soulful accents. But the heavy use of electronic instrumentation and modern studio techniques, plus the presence of some of his brother’s most overtly political lyrics, mark out this album as belonging to Valle’s most adventurous period. On the cover he’s underwater, looking distressed, as though he wants to speak but can’t—a visual metaphor for how suffocated and stressed he felt by the situation in Brazil. By 1975 he was back in the U.S., where he remained in self-­imposed exile until 1980.

Thus ended Valle’s most remarkable burst of creativity. In the 80s, after he returned home, he’d have a similarly fertile stretch, releasing a handful of records with a modern-soul flavor influenced by stateside collaborations with the likes of Leon Ware and Chicago. But when he resuscitated his career yet again in the 90s, he seemed to have lost almost all of his old curiosity and experimentalism. At least U.S. audiences can now hear a reminder of it.