Kelly's Top 40 singles include "Billy Baxter", "Before Too Long", "Darling It Hurts", "To Her Door" (his highest-charting local hit in 1987), "Dumb Things" (appeared on United States charts in 1988) and "Roll on Summer".

Kelly was appointed as an Officer of the Order of Australia in 2017 for distinguished service to the performing arts and to the promotion of the national identity through contributions as a singer, songwriter and musician.

[37] Richard Guilliatt, writing for The Monthly, later described Kelly from a 1979 performance at Richmond's Kingston Hotel, the singer was "a skinny guy with a head of black curls framing a pale face and a bent nose... singing with his eyes closed, one arm outstretched and the other resting on the body of the Fender Telecaster".

[31][45] In an October 1982 interview with The Australian Women's Weekly, Kelly indicated he was more pleased with Manila than Talk as "It has more unity ... with this one we didn't have people dropping into the studio to play.

[10][15] AllMusic's Mike DeGagne felt "While he focuses on life's daily tragedies and tribulations, there is a missing element in the music, as it lacks any vigor or flash".

[31] Russell Crowe, during his first trip to the US, visited the tourist venue of Death Valley and used Post to refocus himself: "[his] concise insights and acerbic wisdom are exactly the music for strolling the bottom of ancient oceans, both literal and metaphoric".

[47] After recording Post, Kelly established a full-time band, which included Armiger, Barclay, and Connolly, bass guitarist Jon Schofield, and keyboardist Peter Bull.

[64] DeGagne observed a style similar to Elvis Costello and Steve Forbert, and said the album provided "acoustically bright story songs and character-based tales with unlimited substance".

[69] Forster stated that, with "Everything's Turning to White", Kelly shows mastery in condensing a Raymond Carver tale of fishermen who discover a dead woman's body but continue to fish before reporting their find.

[56] Paul Kelly and the Messengers' final album, Hidden Things, was a collection of previously released B-sides, stray non-LP tracks, radio sessions, and other rarities.

[31] AllMusic's Brett Hartenbach noted that Kelly's band had fleshed out his songs in the studio, but he was still able to show "his vignettes of life, love, and the underbelly of both have plenty of power on their own".

[31] This line-up issued the CD-EP How to Make Gravy, with the title track earning Kelly a 'Song of the Year' nomination at the 1998 Australasian Performing Right Association (APRA) Music Awards.

[97] APRA's Debbie Kruger noted Kelly's "attraction to the theatrical" where the same protagonist is described in "To Her Door", "Love Never Runs on Time" (from Wanted Man) and "How to Make Gravy".

[105] Songs were written jointly by all group members and their work was a more groove-oriented style compared to Kelly's usual folk or rock formula, using samples, synthesiser and percussion.

[107] During the 2000s Paul Kelly worked as a composer for film and TV scores and soundtracks, including Lantana (also as a member of Professor Ratbaggy), Silent Partner, and One Night the Moon in 2001, Fireflies in 2004, and Jindabyne in 2006.

Finally, One Night the Moon included Mairead Hannan's "richly melodic Irish airs" which "beautifully counterpoint Kelly's work" and Carmody's "distinctive ballads".

[124] Between August and November Kelly performed a series of acoustic shows in New Zealand, the United Kingdom, Ireland, Spain, and France (the latter supporting Ani DiFranco).

[150][151] On 8 October Paul Kelly and the Boon Companions, Hoodoo Gurus, and Sime Nugent performed at the Athenaeum Theatre in Melbourne to again raise funds for Life, Love and Health, and to help support their ongoing programs in Timor-Leste in response to the needs of the people during the humanitarian crisis.

[156][157] In November–December Kelly undertook his A-Z tour, a series of solo acoustic performances playing 100 of his songs in alphabetical order over four nights, at the Brisbane Powerhouse, Melbourne's Spiegeltent, and at the Sydney Opera House.

[160][161] Kelly made his first appearance at the Big Day Out concerts across Australia in early 2008,[162] while in March he performed at the South by Southwest music festival in Austin, Texas.

[173] Also performing at the Melbourne concert were Augie March, Bliss n Eso with Paris Wells, Gabriella Cilmi, Hunters & Collectors, Jack Johnson, Chambers and Shane Nicholson with Troy Cassar-Daley, Kings of Leon, Jet, Midnight Oil, Liam Finn, Split Enz, and Wolfmother.

[174] On 13 and 14 November, radio station Triple J presented a Kelly tribute concert—marking his 30th anniversary as a solo artist—at the Forum Theatre in Melbourne, and highlighted his contribution to Australian music.

The line-up included Missy Higgins, John Butler, Paul Dempsey (Something for Kate), Katy Steele (Little Birdy), Bob Evans, Ozi Batla (The Herd), Dan Kelly, Clare Bowditch, Jae Laffer (The Panics), Adalita Srsen (Magic Dirt), Dan Sultan, and Megan Washington interpreting Kelly's songs, with members of Augie March as the backing band and Ashley Naylor as musical director.

[180] The related audio book on 16×CDs has Kelly joined by Australian actors, Cate Blanchett, Russell Crowe, Judy Davis, Hugh Jackman and Ben Mendelsohn each reading a chosen chapter.

[186][187] In April 2011 Kelly performed at the East Coast Blues & Roots Music Festival (Bluesfest), which was followed by appearances as a special guest at Dylan's concerts in Sydney and Melbourne.

[198] After it appeared on ABC-TV in October of the following year, Andrew P. Street of The Guardian noted it "brings an ambitious, complex young Kelly to life – making a relisten of his work essential".

"[1] Fellow songwriter Neil Finn (Crowded House) has said, "There is something unique and powerful about the way Kelly mixes up everyday detail with the big issues of life, death, love and struggle – not a trace of pretence or fakery in there".

[215] Tim Freedman (The Whitlams) acknowledges Kelly, Peter Garrett (Midnight Oil), and John Schumann (Redgum) as inspiring him by "[furnishing] our suburbs with our own myths and social history".

[73] The Monthly's Richard Guilliatt travelled with Kelly, his band and "his new love and future wife, the diminutive" Fairfax on a section of the group's US tour prior to the release of Under the Sun.

[239] Kelly was appointed as an Officer of the Order of Australia in 2017 for distinguished service to the performing arts and to the promotion of the national identity through contributions as a singer, songwriter and musician.