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He has been a full-time jazz musician since 1 January 1977, and Fairweather worked part-time for seven years before that with local jazz bands in Essex and London. He recorded his first album in 1975 with trumpeter Alex Welsh's band, as deputy for Welsh. After turning professional, Fairweather helped found pianist Keith Nichols' "Midnite Follies" Orchestra, also performing with Nichols in his "Ragtime Orchestra" and on a tribute show to Fats Waller. He performed with several other bands, including one led by drummer Lennie Hastings. Starting in 1978, he recorded solo albums, and joined a quartet known as Velvet, with guitarists Denny Wright and Ike Isaacs plus bassist Len Skeat.
In 1979, Fairweather became co-director of the non-profit charity 'Jazz College' with pianist Stan Barker. He also joined the Pizza Express All Stars (l980–82). In 1983, he began leading groups of his own and helped to revitalise the Kettners Five, co-leading the group with double-bassist Tiny Winters. Fairweather and Winters collaborated in 1983 on a touring tribute to trumpeter Nat Gonella, and they worked on various other projects together over the next decade. Fairweather's musical style has been influenced by a number of artists, particularly Louis Armstrong, Ruby Braff, Billy Butterfield, Bobby Hackett, Red Nichols and Gonella. Digby’s Half Dozen was formed in 1995, and they toured and recorded with singer George Melly in the later years of his career (2003–2007). Thereafter, Fairweather's group toured with former Manfred Mann lead singer Paul Jones in their presentation titled 'Rocking in Rhythm' (2007–present).
Apart from his playing and group leading, Fairweather has long pursued a parallel career as a jazz broadcaster and writer. From 1985 to 1988, he worked and recorded with Brian Priestley's Special Septet and Tony Milliner's Mingus Music, and wrote the book How to Play Trumpet. By 1990 he had embarked on a dual vocation as broadcaster for BFBS, BBC World Service, Jazz FM (1991–92) and BBC Radios 2/3 (1992–98), including occasionally deputising for Humphrey Lyttelton on his show Best of Jazz and successively presenting Jazz Parade and Jazz Notes. In 1987 Fairweather founded the Association of British Jazz Musicians and the National Jazz Archive. That same year he formed the Jazz Superkings with Dave Shepherd, Brian Lemon, Allan Ganley and others. Fairweather helped bring jazz musicians into the British Musicians' Union by proposing, then founding, its Jazz Section in 1992 (discontinued in 2014). In 1994 (with trombonist Pete Strange), he co-founded The Great British Jazz Band and continues to teach and do solo work. Following the death of Humphrey Lyttelton, he was invited to succeed Lyttelton as the patron of the Birmingham International Jazz Festival. In 2015 he continues to lead his Half Dozen (winners of the Best Small Group category in the British Jazz Awards for 2005/6/8/10/11/12/13/14) and to perform as a soloist. In 2013 he received the Worshipful Company of Musicians Lifetime Achievement Award for Services to Jazz.
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- BBC Jazz Society Musician of the Year (1979)
- Freedom, City of London (1992)
- British Jazz Award (trumpet) (1992)
- British Jazz Award (1992)
- Benno Haussman Award (1993, Cork Jazz Festival)
- Freedom of Southend on Sea (Millennium Role of Honour/2000)
- British Jazz Award: 'Top Small Group' (Digby's Half Dozen) (2005, 2006, 2008–2014)
- Worshipful Company of Musicians London Lifetime Achievement Award for Services to Jazz (2013)
- Havin' fun (Black Lion, 1979)
- Going out stepping (Black Lion, 1979)
- Songs for Sandy (Hep Records, 1981)
- Anytime, any place, anywhere (Hep Records, 1982)
- A Portrait of Digby Fairweather (Black Lion, 1991)
- Mick Potts Tribute Concert (Flat Five Records, 1993)
- Squeezin' the Blues Away (with Tony Compton/FMR Records, 1994)
- The Quality of Mercer (with Susannah McCorkle/Keith Inggham/Jazz Alliance, 1996)
- Twelve Feet off the Ground (with Digby Fairweather Half Dozen/Flat Five Record, 1998)
- Singing and Swinging the Blues (with Half Dozen/George Melly/Robinwood Productions, 2003)
- Things ain't what they used to be (with Half Dozen/Robinwood Productions, 2003)
- The Ultimate Melly (Candid Records, 2006)
- Two Part Conversations (With Craig Milverton/Raymersound, 2006)
- Partners in Time (With Pete Strange/Rose Cottage Records (RCR 001), 2006)
- Farewell Blues (with Half Dozen/George Melly/Lake Records, 2007)
- Jazz at the Stone Hall (with Dave Claridge New Orleans Band)/Rose Cottage Records (RCR 002), 2009)
- 'Thirty Five Not Out' Rose Cottage Records (RCR003)
- Crackerbarrel Music (Hainault Records, 2011)
- 'Chris Ellis:vocal with hot accompaniment' (Digby Fairweather Archives) Rose Cottage Records (RCR005)
- To Frederick with Affection (Rose Cottage Records (RCR 004), 2012)
'The Best of Digby Fairweather's Half Dozen' Rose Cottage Records (RCR 007)
- Fairweather, Digby (2002). Notes from a Jazz Life. London: Northway Books. ISBN 978 0953704019. (autobiography)
- Fairweather, Digby (2005). Nat Gonella: A Life in Jazz. London: Northway Books. ISBN 978 0953704071.
- Priestley, Brian; Ian Carr; Digby Fairweather (2007). The Rough Guide to Jazz. Rough Guides. ISBN 1843532565.
- 'On the Road with George Melly; the final bows of a legend'JR Books 2007
- 'Notes from a Jazz Life' (2nd edition) Northway Books 2014