Wilmoth Houdini - Okeh 65010 (1929)

From wikipedia...

Frederick Wilmoth Hendricks (November 25, 1895 in Port of Spain, Trinidad and Tobago – August 6, 1977 in New York, New York), best known as Wilmoth Houdini, was a prominent calypsonian.

In 1916 he started his career in earnest when he began working with the African Millionaires, a large carnival group consisting of about 25 members. He arrived in New York City sometime around 1927, after working on cargo ships and travelling extensively. Not long after his arrival there, he began cutting records with local bands for Decca Records, notably Gerald Clark's Night Owls. He released well over a hundred different 78s between 1928 and 1940, also under the names of Fredrick Wilmoth Hendricks (his given name), Edgar Leon Sinclair (the name on his US passport), and King Houdini. His 1939 composition "He Had It Coming" was a hit for Louis Jordan and Ella Fitzgerald under the new title "Stone Cold Dead in the Market". The song stayed on the top of the R&B charts for five weeks, and reached no. 7 on the pop charts. Gaining a good deal of recognition, Houdini wasted no time in organizing high-profile calypso festivals and concerts around New York, quickly becoming a respected member of the Caribbean communities there.

After moving to New York (as one of the earliest Trinidadian émigrés), he was often the object of derision by the calypsonians still in Trinidad, who claimed that he was stealing their ideas and capitalizing on them in the USA. This can be seen in numerous calypsos of the early to mid-1930s, from Roaring Lion and Attila the Hun in particular, who also recorded in New York at the time. This led to Houdini's 1934 rebuttal, "Declaration of War". Towards the beginning of the 1950s he played regularly at the Caribbean Club on Seventh Avenue, New York, with his only real rival, The Duke of Iron, also a native of Trinidad.

Houdini died on August 6, 1977, in New York City, where he had lived for the majority of his life. He is buried in Woodlawn Cemetery in The Bronx, NYC.

Wilmoth Houdini with the Montrose-Barrow String Band.

Recorded in New York on March 25, 1929.

Albert Socarras & His Cubanacan Orchestra - Brunswick 7490 (1935)

Born in Cuba in 1908, Alberto Socarras is credited for having recorded the first jazz flute solo which took place in July, 1927. As a sideman with Clarence Williams' Orchestra, they cut Shooting The Pistol issued on Paramount 12517.

Here's one of two records Socarras made in New York for Brunswick under his own name. I've yet to find a personnel listing and recording date.

1930 New York Age Newspaper

Ramito Con El Autentico Sexteto Borinquen - BMC 15-261 (1960s?)

From wikipedia...

Florencio Morales "Flor" Ramos (September 5, 1915 – February 23, 1989), better known as Ramito, was a Puerto Rican singer, trovador, and composer who was a native of Caguas, Puerto Rico. He is considered the king of Jíbaro music. His brothers Luis ("Luisito") and Juan María ("Moralito") also attained major recognition as jíbaro singers.

Ramito was born in the Bairoa subsection of Caguas, Puerto Rico. "Caguitas" (Little Caguas) was a boyhood nickname of his, used by his closest friends. He left school in fourth grade ("but an old-time fourth grade at that!", he mentioned whenever asked) to assist his parents, who were parenting twelve other children (including six of their own), and whose thereby economic situation was precarious. His mother had been an amateur singer and improviser and he would sing her favorite songs at the sugar cane fields where he served, first as a water boy and later as a messenger and sugar cane cutter. Regarded as a good singer by his peers, he was already singing for money at the age of thirteen. In 1932 he participated at a local trova singers contest in Caguas. That was the beginning of fame for Ramito.

Ten years later, in 1942, he inaugurated the WIAC radio station, a station with national reach. He also sang in the inaugural broadcast of WKJB-AM in Mayagüez, in 1948. Later he animated the radio show "La Hora del Volante", from Bayamón. His affable stage presence and reputation as a fast improviser and bright lyricist earned him a large following in Puerto Rico and growing communities of Puerto Rican migrants to the northeastern United States.

Ramito was featured in the short musical film Truya (1950), along the most reputed Puerto Rican jíbaro singers and musicians of the time, including Jesús Sánchez Erazo "Chuíto El De Bayamón", Ernestina Reyes, "La Calandria", Maso Rivera and others. He also appeared on television multiple times and he released a wide number of trova albums, of which many were best sellers in Puerto Rico and other Latin American countries.

Between 1960 and 1972 he nominally moved to New York, where he worked on the radio show "La Montaña Canta" on the WHOM station. He maintained a constant presence in Puerto Rico, however, virtually living between both places.

Ramito became an icon to fans of trova music in Puerto Rico, specially those in the mountainside areas of that island. He toured intensely in Latin America and the United States, and had a particularly strong following among the Puerto Rican community in Hawaii, which he visited twice. He also visited Okinawa, where he entertained Puerto Rican troops of the United States military who were stationed there. He sang for president John F. Kennedy at the White House on November 1961, in a showcase of Puerto Rican musical talent that complemented a visit by then governor Luis Muñoz Marín to Washington.

A more in depth biography can be found here.