Rea had not played the local music scene around Middlesbrough much, and had no real history of playing with any local bands. However, under the guidance of local club owner, and promoter John B. McCoy he managed to gain a record deal with Magnet Records. Whatever Happened to Benny Santini? was Rea's debut album, released in 1978 (see 1978 in music). The first single lifted from the album, "Fool (If You Think It's Over)", is his biggest hit in the United States, peaking at number twelve on the Billboard Hot 100 and reaching number one on the Adult Contemporary Singles chart. "Fool (if You Think It's Over)" was nominated for a Song of the Year Grammy, losing out to Billy Joel's "Just the Way You Are". Unlike most of Rea's other singles, "Fool..." failed to appear on the UK Singles Chart on its first release and only reached #30 when re-released in late 1978 to capitalise on its US achievement. UK singer Elkie Brooks enjoyed greater success with "Fool.." in 1981 when she charted a single at #17. It was also the first record played by Radio Caroline, after a long period off the air. A cover of "Fool..." by Kenny Craddock was used as the theme for BBC sitcom Joking Apart.

The title of the album is a reference to a name Rea's UK record label (Magnet) had considered christening him with to make him sound more attractive commercially.

Whatever Happened to Benny Santini? was produced by Gus Dudgeon. Rea was reportedly dissatisfied with the final mix of the album; he later went some way to supposedly rectify this to his satisfaction, starting with 1988's greatest hits compilation New Light Through Old Windows, which featured a re-recorded version of "Fool..." and several other of his back-catalogue tracks. Dudgeon went on to produce Rea's next effort, Deltics. It is rumoured within the music-industry however, that this 'dissatisfaction' was merely a clever way of dispensing with royalty, or contractual, payments on the original recordings that would have been due under an agreement with his first Manager John McCoy, with whom Rea had subsequently dispensed.

Rea began to focus his attention on continental Europe, releasing eight albums in the 1980s. It wasn't until 1985's Shamrock Diaries and the songs "Stainsby Girls" and "Josephine" that UK audiences began to take notice of him (on 5 July 1986 Rea played in front of 95,000 people at Slane Castle, Ireland, as a supporting act of band Queen on their Magic Tour). Follow-up albums On The Beach and Dancing with Strangers became big UK hits before the New Light Through Old Windows compilation album in 1988 brought Rea success.

His next full album was to be his major breakthrough. The Road to Hell (1989) enjoyed massive success and became his first number one album in the UK. This accomplishment could not be mirrored in the US, where it only reached #107, in spite of the single track "Texas" achieving extensive radio airplay. The title track was released as a single and reached the UK Top 10. The follow-up album, Auberge, was also a European hit, reaching the top spot in the UK.

After Auberge, Rea released God's Great Banana Skin, which reached #4 in the UK. The album returned Rea to the rockier sound of Road to Hell, and the single "Nothing to Fear" gave him another Top 20 hit. A year later Espresso Logic hit the Top 10 and "Julia", written about his second daughter, gave him his eleventh Top 40 position. A period of ill health meant his next album did not appear until 1998.

Despite no singles being released and little promotion, The Blue Cafe still made the UK Top 10, though it proved to be Rea's last. In 1999, 10 years after Road to Hell, Rea released The Road to Hell: Part 2, which received no promotion and never made the Top 40. However, it didn't get Rea down: in 2000, he released King of the Beach, receiving critical praise and a healthy Top 30 placing.

In 2000 a remix of Rea's 1986 "On the Beach" single by York was released and enjoyed moderate success on the dance floor.

Following a severe bout of pancreatitis, and a predicted 50% chance of survival after an operation called a Whipple procedure (pancreaticoduodenectomy) in 2001, Rea promised himself that if he recovered, he would be returning to his blues roots. This near brush with death was the catalyst for a complete change in musical direction and motivation. The resulting Blue Guitars 11-CD collection of 137 blues-inspired tracks recorded in just 18 months, completed with his own paintings as album covers, is seen by himself as his finest work to date. In an interview with The Britsound Radio Show, Rea revealed that "it’s not until you become seriously ill and you nearly die and you’re at home for 6 months, that you suddenly stop to realise that this isn’t the way I intended it to be in the beginning. Everything that you’ve done falls away and start wondering why you went through all that rock business stuff." So, in 2002, Rea returned to his blues roots, releasing the album Dancing Down the Stony Road following recording sessions in France and the UK. (An abridged version of the album was later released with the title Stony Road.) The album was followed by a DVD of the same name, comprising a "Making of" documentary and footage from a concert in Cologne. Rea set up his own JazzeeBlue label in 2003 to free himself from the pressure of record companies and their expectations. Since then he has released the blues albums Blue Street (Five Guitars) (an instrumental jazz-blues album) and then The Blue Jukebox (another jazz-blues influenced album released to critical acclaim). He has worked with David Knopfler for two albums: Wishbones (2001) and Ship of Dreams (2004).

Chris Rea released his final box-set album, Blue Guitars, in 2005. Consisting of 11 CDs and 1 DVD (Dancing Down the Stony Road), the album is Rea's testament to blues. Each album contains self-compositions, played and performed in a specific subgenre of the blues. The box-set includes a book containing reproductions of paintings by Rea. In an interview with The Britsound Radio Show, Rea declared that this box-set album is a result of his love for the blues: "It’s just my first love. You know if you take music as romance, then blues was my first love you know, it’s my wife. And it’s with me all the time, and I just adore it." This album closes the final chapter of Chris Rea's solo career as he does not intend to make any further solo records. He has stated that he would continue to make records with some of his favourite players under the name The Memphis Fireflies. A double DVD set and a separate double CD set was released in 2006, including live selections from Rea's farewell tour titled The Road To Hell & Back.

In November 2007, Rea announced a new tour and a new album featuring 38 new tracks on three CDs and two vinyls which included a hardback book in the style of a slightly tatty 12" vinyl sleeve. The Return of the Fabulous Hofner Blue Notes (a dedication to the 1960s guitar of the same name) was released in February 2008. In writing the album, Chris dreamed up a band that had never existed — a pastiche instrumental group from the late 1950s called The Delmonts.

The release of the album was followed by a European tour. The band was introduced as "The Delmonts featuring Chris Rea", and played in various venues across the UK, including the Royal Albert Hall in London. The concerts consisted of a mixture of blues-orientated instrumentals and new songs as well as several Rea classics.

His song "Driving Home for Christmas", which originally reached number 53 in the UK charts when first released in 1988, re-entered at number 33 nineteen years later in December 2007, making it the first time the song had made the UK Top 40. In a live interview on the BBC Radio 4 programme “Today” on December 17, 2009 Chris Rea said he wrote “Driving Home for Christmas” many years before he first recorded it. His wife had come down to London to drive him home to Middlesbrough in her little Austin Mini to save money because it was cheaper to drive than travel by train. Inspiration for the song came as she and Chris were stuck in heavy traffic heading out of London with a long drive North to Middlesbrough ahead of them; but at the end of that journey home – and Christmas - were waiting. Chris says "Driving Home to Christmas” is a “car version of a carol” (a view endorsed by the Reverend Dr Ian Bradley and others in the Church of England). Now it’s an all-time classic – capturing as it does the thoughts and feelings of all those drivers who have to work away from their families but for whom there’s that special time of year when, no matter how long the drive, no matter how bad the weather, no matter how slow the traffic, they’re going to make it home.

In October 2009, Rhino released a new 2-disc best of compilation. "Still So Far To Go - The Best of Chris Rea" contains some of his best known hits over the last 30 years, many of them less well known, as well as more recent songs from his "blues" period. There are also 2 new songs "Come So Far, Yet Still So Far to Go" and the ballad "Valentino". The album was Rea's highest charting album in 15 years, reaching no. 8 and staying in the top 50 for 4 weeks, helped no doubt by a TV advertising campaign.

A new studio album is due to be released in mid-2010.