As a child Caldwell studied Speech and Drama with the London College of Music. He attended Wilkinstown N.S. first as his primary education began and later transferred to St.Oliver Plunkett's in Navan for his final year of Primary. From 1988 to 1993 Enda attended Navan Community College now known as Beaufort College Navan where he completed his leaving cert. Though his first passion was for cars and the motor industry Caldwell was always interested in music and broadcasting through his love of drama listening to Pat Courtenay on Energy 103 breakfast with all the characters he created. He DJ'ed his first disco at the age of 14. He studied Radio Production and Journalism at Ballyfermot College of Further Education in Dublin from 1993 to 1995 where he achieved a merit profile in Radio Production and Journalism (Media) with an HND from BTEC.
Caldwell's Media career began with helping out at Atlantic 252 as an assistant to Tony West. In 1991 he went on to do a course in Television with Navan Community Television now known as Province 5 Television. He also presented actual broadcast programmes for the TV Station such as "The Province 5 Top 5" with Xtravision which was a weekly Video review produced exclusively for the station. His radio career began on Irish pirate radio in 1992 at Kiss FM in Dundalk. Later in 1994 Enda presented some Friday afternoon shows for "Dublin's Dance Music Factory" Sunset 107, as Enda Story. He and Greg Parke were instrumental in establishing Navan's Energy Radio on 1 October 1994.
After graduating from BCFE, Caldwell worked evenings at Tipp FM in Tipperary, WLR FM in Waterford and LMFM in Louth and Meath before debuting at Wexford's radio station South East Radio in 1997 with "South East Radio's Power FM." He worked briefly at Q102.9 and Midlands 103 before moving to Kiss 106 (Northern Ireland) where he launched the station's live programming and co presenting its first ever live breakfast show from December 1.
In late 1998 he played the hospital porter in Angela's Ashes, a 1999 film based on the memoir of the same title by Frank McCourt. It was directed by Alan Parker and starred Emily Watson, Robert Carlyle, Joe Breen as young Frank. Enda is to be seen pushing the hospital trolley with Joe Breen as young Frank after his character develops appendicitis.
Caldwell was later to become Head of Production at the satellite station Radio Limerick One and RLO TV, based in Limerick. In late 1999 and early 2000, Caldwell was also DJing live at many venues across Ireland.
In February 2000, John O'Hara hired Caldwell as the overnight presenter with the newly relaunched Atlantic 252. Caldwell earned an international reputation working for RTÉ and RTL Group for almost two years, presenting every possible shift on the station. His work there included the final live drivetime show from their studios at Mornington House in County Meath on Thursday 20 December 2001, at approximately 4.55pm this was followed by a specially compiled Tribute show produced by Enda Caldwell and Eric Murphy celebrating the station's 12-year history of broadcasting and featuring classic airchecks and playlist tracks from each year of Atlantic 252's history.
For the next several years, Caldwell worked at a number of radio stations in the United Kingdom and Ireland, including Today FM, where he most notably launched Planet Hits the "Saturday Night Hitmusic show" on 26 May 2001 and later went on to present key shifts on the station. He also regularly filled in for Tim Kelly on The Today FM Top 40. In 2003, Caldwell launched the very first "Nothin' but 90's" show on Today FM and presented that show for over two years. He has also presented mainstream daytime shows for Sunshine Radio, Sant Antoni Ibiza, Cool FM, Wyvern FM, Beat 102-103, Kiss 100, Xfm, Real Radio, Reading 107 and Dublin's Country Mix 106.8 before moving to Luxembourg to work for Radio Luxembourg.
On 26 September 2006, Caldwell moved to Luxembourg to take up a programming and presentation position at the newly relaunched Radio Luxembourg.
From July to December 2008 Enda hosted Drivetime at Riviera Radio in Monaco. From 2005 to 2008 has been heard on Kevin Branigan's temporary licensed stations easy-listening 92.1 Choice FM and The Rock 94.9 The Rock where he presented "The Classic Album at Midnight". Enda also was involved in other temporary licensed stations: The Word, Christmas FM, Hot Country, Real Radio, Heartbeat FM and some 90's shows on The 90's Network.
Since 1993 Caldwell has operated his own Freelance voice-over and Media business Enda Caldwell Productions.
From 2013 to 2017 he was the male S&P Voice of Dublin's New Sunshine 106.8. Previously he was the male station imaging voice of Beat 102-103. Before that from September 2006 until March 2008 Enda was the evening imaging voice of The Download Chart on The Fridge for Dublin's Hitmusic Station FM104. He has also voiced radio imaging for other stations including Galway's 958 (an opt-out service for Galway Bay FM, Iur FM in Newry as well as other imaging for stations like Peak Hill FM 89.5 in Peak Hill Central NSW Australia, Eldo Radio in Luxembourg and his voice has been heard on MCM's Gold Network in Australia as a holiday speciality Imaging voice on The Jono And Dano Show.
In 2008 Enda played a character voice for an Italian children's cartoon animation called "Pipi Pupu and Rosemarie" penned by the Oscar award winning screenwriter Vincenzo Cerami for syndication with BBC, on Canadian TV and many other outlets internationally.
Caldwell worked as a cover presenter on Dublin's FM104 from October 2010 and until May 2012 he also worked briefly Sunday afternoons and a regular fill-in on Wicklow's radio station East Coast FM February to December 2011.
On 3 December 2012, Caldwell also assumed an evening DJ position on "DSN Hits", an internet radio station broadcasting from Alliance, Ohio in the United States. He then moved to the midday (US Eastern Time) position, before leaving the station on 7 May 2013.
In August 2013 Enda joined the team at New York's Only Dance Station Pulse 87 where he is part of the regular weekday line-up. He continues to do freelance TV Continuity in addition to his radio work. On 24 June 2014, KYLI Las Vegas announced that it has ended its three-year partnership with Jelli 96.7FM. On 25 June, the station adopted the Pulse 87 Dance/EDM brand and relaunched as "Pulse 96.7," . The Pulse 87 brand will continue to be offered online. Enda hosts 7pm to Midnight Monday to Thursday on Pulse 87 NY & 96.7 FM Las Vegas in addition to shifts at The New Global Radio The Official English Speaking Station on the Costa Del Sol.
Since 2016 Enda is now the European Representative for www.allaccess.com based in Malibu Beach, California.