Australian musicologist, Ian McFarlane, described him as a "permanent fixture of the pub/concert/festival circuit and was praised for his vocal abilities" as "one of the best soul singers working in Australia" during the 1970s.
[2] De Castro relocated to Sydney in 1969 and joined The Browns, alongside Ray Arnott on drums (ex-Chelsea Set), Ronnie Peel on bass guitar (The Missing Links, The Pleazers, Rockwell T. James and the Rhythm Aces, the La De Da's) and Les Stacpool on guitar (Chessmen, Merv Benton and the Tamlas).
[5] De Castro also appeared at the 1970 Ourimbah "Pilgrimage for Pop", Australia's first rock festival,[6] and was included in the 2012 film Once Around the Sun, a psychedelic movie about the event.
"[4] The group broke up in September and de Castro formed a briefly existing band, Flite, with Capek on piano (by then ex-Carson), Barry Harvey on drums (Thursday's Children, Wild Cherries, Chain, King Harvest), Vince Melouney on guitar (Billy Thorpe and the Aztecs, Bee Gees, Fanny Adams, Cleves) and Barry Sullivan on bass (Thursday's Children, Wild Cherries, Chain, Carson).
He was joined by former bandmates Kennedy, MacKenzie and McGuire; and new associates Tim Martin on saxophone and flute, and Charlie Tumahai on vocals and percussion (Healing Force, Chain).
[9] In August 1972 Friends released a single, "B-B-Boogie", which Duncan Kimball of MilesAgo website felt was a "solid boogie-rock number highlighted by Green and Oliver's dexterous dual guitar work.
[11] Kimball preferred the B-side, "Freedom Train", which he opined was a "driving, prog-jazz" track that "became their signature tune", it was "one of the best Australian progressive recordings of the '70s.
[10] Tumahai returned to Healing Force in January 1973 and, late that month, Friends appeared at the Sunbury Pop Festival as a six-piece – de Castro, Green, Kennedy, Martin, McGuire and Oliver.
[12] On stage at Sunbury de Castro joined Lobby Loyde and the Coloured Balls, and Billy Thorpe for an early morning session.
[8][10] In June Leo de Castro and Friends disbanded when Burton, McGuire & Kennedy all left to form an eponymous trio.
[8] That group's lead single was a cover version of "Lady Montego", which also appeared on their debut album, Big Red Rock (November 1974).
[3] Late in 1974 de Castro, on vocals, joined the Sydney-based group, Johnny Rocco Band, alongside Tony Buchanan on saxophone (Thunderbirds, Daly-Wilson Big Band), Russell Dunlop on drums (Aesop's Fables, Levi Smith's Clefs, Mother Earth), Tim Partridge on bass guitar (Clockwork Oringe, King Harvest, Island, Mighty Kong), Harris Campbell from Arapae, Te Kuiti on guitar and vocals, and Mark Punch on guitar and vocals (Mother Earth).
[16][17] During 1988 de Castro recorded live-in-the-studio for an album, Long White Clouds, using two disparate backing groups, Roger Janes Band and The Dancehall Racketeers.
[3] In a seachange mood, to further demonstrate the diversity of his musical palette, Leo de Castro and the Cuban Heels were formed in Hobart in late 1989, with Steve 'Keys' Grahame on piano/keyboards, Marcus "Piz" Pizzolato (ex Mary Lou and the Brokenhearted) on lead guitar, Mick 'Moonie' McCallum (ex Rainbow Stew) on pedal steel, Simon Gethen (ex Albino Spade/Tim Brewster and the Blues Roosters) on bass, and Dennis Matthews (ex Sydney Clubs/Mary Lou and the Brokenhearted) on drums.
Shofield described de Castro, "[he's] not a well man, so the siren song of home and family is calling him away from Tasmania after more than 20 years of playing music here.
[20] In February 2012 Radio New Zealand National's Musical Chairs aired a two-part episode, "Leo de Castro – The Elusive Legend".
[17] The reporter, Keith Newman, interviewed de Castro, Ray Oliver (bandmate), Bob Burns (promoter) and Evan Silva (soul singer).