1958: Harry Webb and the Drifters made a concert appearance at the Regal Ballroom in Ripley.
Later Harry Webb changes his name to Cliff Richard.

1959: On May 2nd, Cliff Richard appeared on ‘Oh Boy!’, Cliff sings “Dynamite”, “Turn Me Loose”, “Choppin’ ‘N’ Changin’, duets with Marty Wilde on “Tell Him No” and duets with Alma Cogan and Marty Wilde on “That’s Love”.
Cliff Richard first E.P. “Serious Charge” (SEG 7895) is released.
Cliff’s 4th single “Mean Streak” / “Never Mind” (DB 4290) released and enters the British charts, “Never Mind” the song on the B-side, also enter the charts the following week.
May 14 th, Cliff Richard's first film "Serious Charge" premieres in London.
The film stars Anthony Quayle, with Cliff featuring as a young semi-delinquent trying to make it as a rock singer.
Cliff Richard breaks entirely new ground on May 9th, when he makes his first appearance on BBC TV.
Cliff Richard becomes the first pop singer to star in two BBC TV shows on the same night.
On May 23rd, Cliff Richard appeared on ‘Oh Boy!’, Cliff sings “Mean Streak”.
Cliff Richard appears on the final ‘Oh Boy!’ show on May 30th, he sings “T.V. Hop” with Marty Wilde, Billy Fury, Bill Forbes & Dickie Pride, “Turn Me Loose”, “Three Cool Cats” duets with Marty Wilde and Dickie Pride, duets with Marty Wilde on “Early In The Morning” and with Lord Rockingham’11 on “Lonesome Traveller”.

1960: Cliff Richard has again been chosen for the ‘Royal Variety Show’.
Cliff Richard’s Sunbeam Alpine, disappears in Derby and turn up 300 miles away in Dundee.
Cliff Richard appears on the ‘Royal Variety Show’; other artists are Russ Conway, Diana Dors, Lonnie Donegan, Max Bygraves, Adam Faith, Nat King Cole and Billy Cotton.
Cliff Richard’s nationwide series of one-night-stands comes to an end at Clacton Essoldo.
Cliff Richard’s discovery Dave Simpson enters the chart with “Sweet Dreams”
Cliff Richard bought a new house for his parents in Winchmore Hill, North London.
May 21st, Cliff Richard and The Shadows appeared on the ATV 'Saturday Spectacular', Cliff sings “A Teeneagner’s Romance” ,”Twenty Flight Rock”, “Kansas City”, “Willie And The Hand Jive”, “Fall In Love With You” and “Mean Woman Blues”, Bobby Rydell is his guest on the show.
Columbia invited Cliff’s fans to choose Cliff’s next single, “Please Don’t Tease” was chosen.

1961: Cliff Richard and The Shadows appear at ‘NSPCC Pied Pepper Ball’, Princess Margaret, who attends with her husband requested Cliff’s appearance.
“Listen To Cliff” (SX 1320 (MONO) / SCX 3375 (STEREO) 4th album from Cliff is released.
Cliff Richard and the Shadows to starred in their new film “The Young Ones”.
May 15th, Cliff Richard’s father Rodger Webb died at the age of 56.
Cliff Richard goes to the ‘Variety Club Awards’ dinner at the Dorchester, London.
Cliff Richard and The Shadows attend a special event organized by the ‘Variety Club’ at the Festival Gardens, London.
Cliff Richard and The Shadows made their first appearance on ITV’s ‘Thank Your Lucky Stars’.
Cliff Richard presents awards at the Methodist Association of Youth Clubs’ annual get-together at the ‘Royal Albert Hall’ London, Cliff sings “Living Doll”.
South African Carole Gray, a dancer in the stage musical ‘West Side Story’, is signed up to play Cliff’s girl friend in “The Young Ones”.

1962: Cliff Richard’s new single “I’m Looking Out The Windows”/“Do You Wanna Dance” (DB 4828) released.
The single is double sided hit and enters top ten in the British charts.
Cliff Richard and The Shadows signed to ‘Leslie Grade Organization’.
E.P. “Hits From The Young Ones” (SEG 8159 Mono) is released.
Cliff Richard and The Shadows appeared on “Thank Your Lucky Stars”.
Cliff Richard presented with ‘Gold Disc’ for “The Young Ones” and The Shadows for “Apache”, others artists on the show are Eden Kane, Joe Brown, The Vernons Girls and Candy Sparling.
Cliff Richard appears on ‘Our Friends the Stars’ charity show at London’s Victoria Palace.
Cliff Richard, The Shadows and Norman Vaughan appeared in a cabaret show for civic reception for Leyton Orient Football Club.
Laurie Peters will co-star with Cliff in “Summer Holiday”.
Cliff Richard & The Shadows fly to France to watch Ray Charles in concert at Paris Olympia.
Cliff and The Shadows along with other artists fly to Greece to commence shooting for “Summer Holiday”.

1963: Cliff appears on ‘The Star Show’ was recorded for BBC, but this program was never broadcast.
Cliff and The Shadows broadcast from Paris Olympia on ‘Europe One’ radio show.
In Barcelona, Cliff recorded songs in Spanish for his new LP “When In Spain”.
“Lucky Lips” / “I Wonder” (DB 7304) released.
E.P. “Holiday Carnival” (SEG 8246 Mono) / (ESG 7892 Stereo) is released.
“Summer Holiday” is at No.1 in Norway and at No.2 in Hong Kong and at No.10 in South Africa.
“Bachelor Boy” is in Top Ten in Hong Kong, Malaysia and South Africa.
“Dancing Shoes” is Top Ten in India, South Africa and Thailand.
‘Life with Cliff Richard’ is published.

1964: Cliff Richard on German TV show in Munich.
E.P. “Cliff's Palladium Successes” (SEG 8320 Mono) is released.

1965: E.P. “Look In My Eyes Maria” (SEG 8405 Mono) is released.
Cliff Richard recorded 20 songs in Lisbon, 6 songs in English and 14 songs in Italian for his new LP “When In Rome”.

1966: “Kinda Latin” (SX 6039 MONO) / (SCX 6039 STEREO) is released.
Cliff Richard sings “I Could Easily Fall (In Love With You)”, “Blue Turns To Grey”, “The Minute You’re Gone”, “Angel” and “Bachelor Boy” on BBC TV’s ‘Let The Good Times Roll’.
In Poland and Thailand "Blue Turns To Grey" is in Top Ten.
Shooting of Cliff Richard’s sixth film, “Finders Keepers” starts at Pinewood Studios.

1967: E.P. “Cinderella” (SEG 8527 Mono) is released.
Cliff appears on Saturday Club’s 450th edition and sings “Hang On To A Dream”, “Move It”, “Baby It's You” and “Dizzy Miss Lizzy”.
Cliff appears at ‘NME Poll Winners’ Concert’ at Wembley, Cliff sings “In The Country”, “It’s All Over”, “Shout” and “Move It”.
Cliff Richard began filming “Two A Penny” at Pinewood Studios.

May 24th, ATV broadcast a Cliff Richard TV special,  backed by the Peter Knight Orchestra, Cliff sings “Move It”, “Hang On To A Dream”, “Meditation”, “Eso Beso”, “Fly Me To The Moon”, “La La La La”, “I’ll Come Runnin’”, “F.B.I.”, “Baby It’s You” and “Shout”.

1968: Cliff appears and sings “All My love”, “The Day I Met Marie”, “Dizzy Miss Lizzy” and “Congratulations” on BBC’s Saturday Club.
Cliff’s “Congratulations” outsells the Eurovision winner throughout the world and becomes the highest selling looser of the Eurovision Song Contest.
“Congratulations” is at No.1 Belgium, Denmark, Finland, Holland, India, Ireland, Israel, Italy, Japan, Lebanon, Malaysia, Norway, Singapore, South Africa, Spain, Sweden, Switzerland and Thailand.
It is also in top ten in Australia, Hong Kong, New Zealand, Taiwan and South Korea.
“Cliff In Japan” (SX 6244 Mono) / (SCX 6244 Stereo) album is released.
Cliff Richard appears at ‘NME Poll Winners’ Concert’ at Wembley, Cliff sings “In The Country”, “Shout”, “Congratulations” and “The Day I Met Marie”.
Cliff is presented with “Top British Vocal Personality” award.
Cliff Richard’s BBC TV’s show, he sings “”My Babe”, “Congratulations”, “It’s All In The Game”, “Feeling Groovy”, “Something Good”/ “If Ever I Should Leave You”, “The Minute You’re Gone”, “The Day I Met Marie”, “Take A Bird Who Can Sing”, “Oh No John No”, “Passing Strangers” duet with Cilla Black, “Big Ship” and “Visions”.

1969: “Big Ship”/ “She’s Leaving You” (DB 8581) released.
Cliff Richard appears at ‘NME Poll Winners’ Concert’ at Wembley, Cliff sings “Good Times”, “Move It”, La La La La La” and “Congratulations”.

1970: Cliff’s 50th single “Goodbye Sam Hello Samantha”/ “You Never Can Tell (DB 8685) released.
Cliff Richard says that his favourite of the 50 singles is “The Day I Met Marie” written by Hank.
Cliff appears at NME Poll Winners’ Concert, singing “The Girl Can’t Help It”, “Great Balls Of Fire” and “Throw Down A Line”.
Cliff Richard is voted 2nd for ‘Best British Male Singer’, 2nd for ‘Best British Male Vocal Personality’ and 3rd for ‘World Male Singer’ in NME reader’s poll.
Cliff plays as Clive Harrington in ‘Five Finger Exercise’ at Bromley New Theatre, for three weeks.
Cliff records contribution for Disney Show for BBC TV.

1971: Cliff Richard plays as James Callinger in ‘The Potting Shed’ at Sadlers Wells Theatre, London.

1972: Radio 1 broadcasts the 100 best-selling records of the last decade; Cliff’s “The Young Ones” is at No.7

1973: “Power To All Our Friends” peaks at No.4 in the British chart, Top Ten in many countries and at No.1 in Holland, Israel, Luxembourg and Sweden.

1974: Cliff Richard’s 62nd single “(You Keep Me) Hangin’ On”/ “Love Is Here” (EMI 2150) released.
Cliff appears on BBC TV’s ‘Mike Yarwood Show’ singing his latest single “(You Keep Me) Hangin’ On”.
Cliff appears on BBC TV’s Nana Mouskouri Show, Cliff sings “Give Me Back That Old Familiar Feeling”, “Constantly” and duet with Nana on “I Believe In Music”.

1975: Cliff Richard receives a presentation from Managing Director of World Record Club; Derek Sinclair for the sale of 40000 of the six records box set “The Cliff Richard Story”, later Cliff receives a Gold Disc for the sale of over 80000 box sets.

1976: On Radio Luxembourg, Cliff Richard previews his latest album “I’m Nearly Famous”.
“I’m Nearly Famous” (EMC 3122) album is released.
“I’m Nearly Famous” peaks at No.5

1977: Cliff Richard tours Australia and Asia.

1979: Cliff Richard attends Local Radio Awards at Grosvenor House Hotel, London, organized by Radio and Records News, Radio Month.
Cliff Richard recorded “We Don’t Talk Anymore” for his next single.

1981: Cliff Richard stars in ‘Rock Special’ at Hammersmith Odeon concert, filmed by BBC TV producer Norman Stone, for the four-part Cliff Richard documentary.
BBC films Cliff, backed by the Fantoms at ‘Hard Rock Café’ in London, Cliff sings “D” In Love.
Cliff is voted No.1 in the ‘Top Pop Star’ in the ‘Sunday Telegraph’ readers’ Poll.
Viewers of Noel Edmonds ‘Swap Shop’ TV show voted Cliff Richard ‘Top Pop Star’.
‘TV Times’ presented an award to Cliff for ‘Most Exciting Male Singer on Television’.
Cliff’s “Give A Little Bit More” releases in USA and peaks at No.39 in the chart.

1982: Cliff Richard and Bill Latham flies to Kenya on behalf of Tear Fund.
“I’m Nearly Famous” (FA 3010) re-issued on FAME Label.

1983: Cliff Richard duet with Sheila Walsh on “Drifting” released.
“Dressed For The Occasion” (EMC 3432) album is released.
“Dressed For The Occasion” peak at No.7 in the Albums chart.

1984: Cliff Richard is filmed in Switzerland for the Golden Rose of Montreux festival.

1985: Cliff Richard flies to Portugal for holidays.
Cliff Richard along with many other artists attends a ‘Guinness Book Of British Hit Singles’ presentation by Norris McWhirter at the
Savoy Hotel for authors Tim Rice, Jo Rice, Paul Gambaccini and Mike Read.
Cliff Richard takes part in BBC Wale's health film ‘Don’t Break Your Heart’.

1986: Third single from the musical ‘Time’, “Born To Rock ‘N’ Roll”/ “Law Of The Universe” (EMI 5545) released.
Cliff Richard’s “Living Doll” (new version) with The Young Ones is at No.1 in Australia.

1989: Interviewed for ‘Radio One’ special, also interviewed by Mike Read, discussing all his singles to date.
Cliff Richard interviewed by Graham Blackstock for the ‘Evening Standard’
Cliff Richard records for ‘Rockline’ with Tim Blackmore.
Cliff appears on BBC TV’s ‘Going Live’ to assist the ‘SOS Presentations’’
Cliff Richard interviewed by Frank Bough for ‘SKY’ satellite TV.
Cliff Richard became the first artist to release his 100th single, “The Best Of Me” / “Lindsey Jane” / “Move It” / “High Class Baby” (12EM 92) and reaches No.2 in the British singles chart.

1991: Cliff Richard attends the ‘Ivor Novello Awards’ lunch.
Cliff Richard attends a reception at NO.10 Downing Street.
Cliff rehearses for ‘World Music Awards’ in Monte Carlo, singing “We Don’t Talk Anymore”

1992: Cliff Richard appears on Dutch television, singing “Some People”, “We Don’t Talk Anymore” and “She’s So Beautiful”.
Cliff’s French album “My Kinda Life” released.
Cliff and other artists appear on Gloria Hunniford’s TV show; Cliff sings “Move It” and “My Kinda Life”.
Cliff flies to Monte Carlo to takes part in the presentation of ‘World Music Awards”.
Cliff Richard appears on French TV, singing “Lucille”.

1993: Cliff Richard, Tim Rice and director Frank Dunlop meet at London’s Langham Hilton to discuss the “Heathcliff” project.
“Human Work Of Art” video shoots at the Rainbow Theatre in London.
Cliff Richard appears on the Dutch TV show ‘Staatsloteris’ singing “Peace In Our Time”.
Cliff sings “Human Work Of Art”, “Never Let Go” and duet with Cilla Black on “That’s What Friends Are For” on Cilla Black's show.

1994: Cliff Richard interviewed on phone with Seattle U.S.A.’s Goldmine magazine.
Cliff Richard’s on the cover of U.S.A.’s ‘Goldmine’ magazine.
Cliff Richard is photographed for his calendar.
Cliff takes part in a live telephone interview with B.B.C. Radio Two.
Cliff interviewed by Gloria Hunniford for Radio Two on the postponement of ‘Heathcliff’.

1995: The musical “Heathcliff” postponed, the show would replace by Cliff’s ‘The Hit List Tour’.

1996: Cliff Richard appears in charity concert ‘Gala Variety Show’ at the Wimbledon Theatre in aid of the Princess Alice Hospice.

2001: Cliff in concert ‘Off The Record’ at The Royal Albert Hall in London, on 12, 13, 15, 16, 18, 20, 22, 23, 25, 27

2002: Lu Lu’s new album “Together” released, includes a duet song by Cliff Richard and Lu Lu “Reunited”, she also duets with some of the legends of pop music on her new album.

2005: On Sunday 1st May, Sir Cliff will sing the final song in ‘The Night of 1000 Voices’ at the Royal Albert Hall, an annual concert of songs from the musicals.
On 8th May, Sir Cliff will be among the guest performers at the VE Day 60th Anniversary celebrations in Trafalgar Square, where he will perform “What Car” his new single and “Sentimental Journey”.
Sir Cliff Richard will be presented with a 'Golden Rose' award at the Rose D'Or music festival in Paris on 16 June.
On Monday, 9th May at 6 pm Cliff Richard will do a signing session at HMV London.
Sir Cliff will pre-record a performance of “What Car” for transmission on GMTV and on The Paul O'Grady Show.
Sir Cliff’s next single from the album will be “What Car” releasing on 9th May. The CD version will feature “Slow Down” and “Sentimental Journey”, the DVD version will include "What Car" (Video of live performance at Leeds Castle), "Something's Goin' On" (Video), exclusive behind the scenes studio footage, and "What Car" (audio).