Chris 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? being Rea's debut album, released in 1978. 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..." was not a great success on the UK Singles Chart, failing to chart on its first release and only reaching number thirty when re-released in late 1978.

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. 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 success could not be mirrored in the U.S., however, where it only reached #107. The follow-up album, Auberge, also enjoyed massive European success, reaching the top spot in the UK.

After Auberge, Rea released God's Great Banana Skin, which managed to reach Number 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 11th Top 40. 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. Many felt Rea had begun to lose his way; the album 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.

Following a severe bout of pancreatitis, and a predicted 50% chance of survival after an operation 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. 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. 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).