Originally launched in March 2010 — and enhanced with 24-bit remastering by Joe Tarantino, along with insightful new liner notes — the series showcases some of the most pivotal recordings of the past several decades by artists whose influence on the jazz tradition is beyond measure.

"Like the previous titles in the series, these are all-time classic recordings by some of the most legendary artists in the history of jazz," says Nick Phillips, Vice President of Catalog and Jazz A&R at Concord Music Group and producer of the series. "Anyone looking to build a collection of timeless, essential jazz recordings could begin by simply selecting titles at random from the Original Jazz Classics Remasters series. Their collection would be off to a terrific start."

The five new titles in the series are:
• Vince Guaraldi Trio: Jazz Impressions of Black Orpheus
• Miles Davis featuring Sonny Rollins: Dig
• Wes Montgomery: Boss Guitar
• Chet Baker Sings: It Could Happen to You
• Bill Evans Trio: Waltz for Debby

Vince Guaraldi Trio: Jazz Impressions of Black Orpheus
Recorded in late 1961 and early 1962 for Fantasy, Jazz Impressions of Black Orpheus — featuring bassist Monty Budwig and drummer Colin Bailey — was Guaraldi's celebration of Brazilian bossa nova for Stateside audiences. Propelled by the surprise radio hit single "Cast Your Fate to the Wind," Jazz Impressions of Black Orpheus is the album that made Guaraldi a household name," says Phillips.

The Guaraldi reissue also includes five bonus tracks — the single version of "Samba de Orfeu," as well as four previously unreleased alternate takes: "Manhã de Carnaval," "O Nosso Amor," "Felicidade," and "Cast Your Fate to the Wind."

"Close to half a century later, the music on Jazz Impressions of Black Orpheus remains as fresh and vibrant as it was when first heard in the spring of 1962," says Derrick Bang, author of the new liner notes for the reissue. "The album has remained in print the entire time: no small thing, in an era when all music has a much greater risk of becoming ephemeral."

Miles Davis featuring Sonny Rollins: Dig
Miles Davis and Sonny Rollins recorded Dig for Prestige in October 1951, with help from alto saxophonist Jackie McLean, pianist Walter Bishop, bassist Tommy Potter, and drummer Art Blakey. The reissue features two bonus tracks, "My Old Flame" and "Conception."

"Miles Davis and Sonny Rollins form one of the most empathetic and powerfully moving duos in jazz," says Ira Gitler in his original liner notes. "Although they had recorded together before ("Morpheus," "Down," "Whispering," "Blue Room"), this was their first chance to stretch out together on records." This extra room was made possible via the advent of the LP, which allowed for longer tracks and lengthier solos. "Looking back," Gitler writes nearly six decades later in his new liner notes for the reissue, "the new latitude attitude sometimes led to LPs with some interminable solos, but for the most part it gave extremely creative players and writers a chance to fully speak their minds and hearts. Dig passes the half-century plus test."

In addition to changes in recording technology, the significance of this recording is also about changes that were taking place in the music itself. "The early '50s was a period in which a stylistic progression from bebop to what became known as hard bop was happening," says Phillips. "So this is a snapshot of two artists who would later become absolute legends, making music history together in what was an important transitional period for both of them."

Wes Montgomery: Boss Guitar
Recorded in April 1963 for Riverside, Wes Montgomery's Boss Guitar features Mel Rhyne on Hammond B-3 organ and Jimmy Cobb on drums. In addition to the eight original tracks, the reissue also includes three bonus tracks: alternate takes of "Besame Mucho," "The Trick Bag," and "Fried Pies."

"I think most jazz fans and guitar aficionados would agree that Montgomery was at the peak of his creative powers during his Riverside period," says Phillips. "Clearly the musicianship and the virtuosity that's on display in Boss Guitar leaves no doubt as to why his guitar playing continues to be so influential."

Journalist Neil Tesser, who penned the new liner notes to the reissue, suggests that Montgomery "inspired something close to deification among his fellow guitarists." While the title Boss Guitar was originally a reference to Montgomery's excellent guitar chops, it has taken on a new meaning in the intervening decades. "These days," says Tesser, "I think of it as a nickname for Montgomery himself: an accurate and respectful way of denoting the guitarist who, in the brief and shiny playground called the '60s, unexpectedly found himself calling the shots, leading the way, and – in his wholly unprepossessing manner – letting the jazz world know who was in charge on the instrument he played."

Chet Baker Sings: It Could Happen to You
Recorded in August 1958 for Riverside, Chet Baker Sings: It Could Happen to You spotlights Baker's vocals as well as his trumpet playing. It also features his first scatting on record. Backing him on this date are pianist Kenny Drew, bassists George Morrow and Sam Jones, and drummers Philly Joe Jones and Dannie Richmond. The reissue includes four bonus tracks: "While My Lady Sleeps" and "You Make Me Feel So Young," and previously unreleased takes of "Everything Happens to Me" and "The More I See You."

"It's very easy to tell that the vocalist and the trumpet player on this record are the same person," says Phillips. "Stylistically, Baker's vocal approach — the nuances and phrasing — is very similar to the relaxed, effortless way he plays trumpet, and by the same token, there's a certain lyrical quality to his trumpet playing."

Despite Baker's rocky personal life, he's at the top of his game creatively on this recording. "Here is Chet Baker at 29, smack in the middle of the New York scene," says jazz journalist Doug Ramsey in his liner notes for the reissue. "He is in good musical company and good spirits, beautifully singing a dozen great songs. His playing, particularly when he uses the Harmon mute, indicates an awareness of Miles Davis, but Baker's style and individuality make it impossible to take him for anyone else. As always in Chet's life, there was tumult and trouble, but when it came time to create, the strength of the artist overcame the weakness of the man."

Bill Evans Trio: Waltz for Debby
Captured live at the Village Vanguard in June 1961, Waltz for Debby is the last recording of Bill Evans's classic lineup of bassist Scott LaFaro and drummer Paul Motian (LaFaro was killed in a car accident less than two weeks after these performances). Bonus tracks on the reissue include the Evans Trio's rendition of Gershwin's "Porgy (I Loves You, Porgy)" and alternate takes of "Waltz for Debby," "Detour Ahead," and "My Romance."

"This is one of Evans's most popular and critically acclaimed recordings, and for good reason," says Phillips. You could easily make the argument that Waltz for Debby was not only the high point in Evans's career, but it also set a benchmark for the jazz piano trio format that has yet to be surpassed."