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Dear Jessie


Released: 16.12.89                 Highest Chart Position: 5                     Weeks on Chart: 9                    Total Sales: 255,000

After the more obvious commercial tracks had been lifted from 'Like A Prayer', opinion differed on both sides of the atlantic as to which track should be the final release. While the US opted for the ballad 'Oh Father', the UK opted for the more quirky choice of 'Dear Jessie', probably helped by the fact that the UK appreciates a more novelty-style record, particularly at Christmas.  And this would appear to have been the better choice as 'Oh Father' stalled at No.20 in the US while 'Dear Jessie' peaked at No. 5 in the UK, thereby continuing Madonna's unbroken run of Top 10 hits.  

Written and produced by Madonna and Patrick Leonard, the song was inspired by Leonard's daughter Jessie.  While recording of the title track was going on at Jonny Yuma Studios, Patrick Leonard had to pick up his daughter Jessie from school and since his wife was out of town, had to bring her back to the studio. Madonna, who was initially angry with Leonard for his late arrival, struck up a rapport with Jessie. She commented:

"It was like as if I was my mother and [she] was me. We were playing in our backyard again." 

Witnessing their connection, Leonard approached Madonna with a song he had written for his daughter, titled "Dear Jessie". Madonna changed some of the lyrics and agreed to record the track for Like a Prayer; it was finished within the next three days.

The single cover used a photo from 1987, taken by Herb Ritts.  It showed Madonna in bed, clutching a bed sheet to her bosom and sporting a pair of Minnie Mouse ears. The photo was a reference to the early criticism of Madonna's work, when reviewers described her voice as "Minnie Mouse on helium".  As the  release of "Dear Jessie" was limited to the UK, certain other European countries, Australia and Japan it did not come with a big budget video.  Instead the video combines live action and psychedelic animation, portraying a little girl waking up in bed and interacting with fantasy characters. Madonna herself only appears in the video as an animated fairy.

UK Variations and Collectables

'Dear Jessie' was released in standard 7", 12", cassette single and CD single.  It was supplemented with a limited edition 7" picture disc and a limited edition 12" posterbag.

The 7" vinyl single was issued as standard UK and German pressings which, for once, have no variations.  However there was instead a surprising return to issuing a limited edition 7" picture disc although round rather than shaped.

The 12" comes as a standard UK pressing and also a German 12" which is surprisingly rare.  It normally sells for £15-£20.  It is fair to say that the German 12" is harder to track down than the limited edition poster-bag which is readily available.

'Dear Jessie' also marks a shift away from 7" singles when it comes to issuing top-ups as for the first time it is the cassette single which appears in two versions, one with just a 'Sire' logo and a second with both 'Sire' and 'WB' logo. 

The CD single also appears in two versions.  The standard release marked the debut of the new 5" format which would be the standard from hereon for all Madonna CD singles.  However, there is also an extremely limited 'picture CD' whereby a colour image is pressed into the CD itself.  This CD is either extremely limited perhaps due to being expensive to produce or it was rumoured, it was withdrawn on the first day of release.  The contributor to this site bought a copy direct from a record shop which would imply that it was not withdrawn, just issued in extremely low numbers.  

It is not surprising that this item - which is by far the rarest of all Madonna CD singles - is the centrepiece for this release.  Although there is no doubting its rarity, it is almost constantly available on Ebay albeit at eye-watering BIN prices of up to £350.  

Promotional Items

'Dear Jessie' comes with an interesting mix of rare promos and test pressings. Aside from the usual 7" in stickered sleeve it also appears to be the first CD single issued with the same circular promo sticker as the standard 7".  Perhaps this was to promote the shift to CD singles, in particular the new 5" format.

Among the rarest of all the test pressings are two that exist for the 7" picture disc - white vinyl and clear vinyl.  The existence of a clear vinyl suggest an early intention to have a clear background around the shape of Madonna's mouse-eared head, or possibly another shaped picture disc, but this was rejected in favour of the full circle with white background. 

In addition, a special promo cassette exists in a special custom pink sleeve with a 'Roy' catalogue number. According to the contributor, this particular cassette was only pressed up for employees during a sales conference - and 'Roy' was the area sales manager! Unlike the standard blue cassettes, this item was never intended for distribution to record shops and is, accordingly, one of the rarest promotional cassettes.  

In terms of paper-based items, 'Dear Jessie' sees a return to the counterstand displays, but not, apparently, display flats.  There are also three different music press adverts to collect, the later of which being quite hard to find as it was only selectively issued to the more 'mature' magazines such as 'Vox' and 'Q' as it's intention was to reach a more 'adult' audience.  The advert itself was more about promoting Madonna as "The 'Face of 80s - and the 90s'" and the LP 'Like A Prayer' rather than the single. 


ALL PROMOTIONAL ITEMS CAN BE VIEWED IN THE PROMO SECTION - FOR ITEMS RELATING TO THIS RELEASE CLICK HERE

7" Single - Standard Release

7" Single - Standard Release with indented label 

7" Single - German pressing for UK release

7" Single - Limited edition picture disc (in barcode stickered sleeve)

7" Single - rare test pressings in both white and clear vinyl

12" Single - Standard Release

12" Single - German pressing (with UK catalogue number)

12" Single - Limited edition posterbag

Cassette Single: Two Versions

CD Single - Standard 

CD Single - Extremely limited picture disc (withdrawn?)


This is a webpage created purely by collectors for collectors, and is not endorsed by Boy Toy Inc., Geffen Records, Madonna, Maverick, Sire, or Warner Music Group. All logos, images and pictures on this site are the property of their respective owners.

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