On December 16 1989, Dear Jessie debuted at #9 on the UK Singles Chart.
The single would climb to its peak position of #5 on December 30th, where it remained for three weeks before beginning its descent.
On April 2 2005, Madonna was featured in Q magazine as one of the Five Essential Acts in Music, along with The Beatles, Bob Dylan, U2 and The Velvet Underground.
Q magazine listed Like A Prayer as her definitive album:
If you only buy one album….Like A Prayer. Always more interesting when not seeking novelty, Madonna hit artistic and commercial gold with Like A Prayer, her best and least contrived album. The title track, all swirling choruses and kitchen – sink production, remains her major statement, but Express Yourself was ferocious dance, while on the rarely lauded Dear Jessie she had never sounded so human.
Q magazine also listed what they considered to be Madonna’s essential singles:
Holiday, Borderline, Material Girl, Like A Virgin, Crazy For You, Into The Groove, Papa Don’t Preach, La Isla Bonita, Open Your Heart, Live To Tell, Who’s That Girl, Causing A Commotion, Vogue, Justify My Love, Ray Of Light, Frozen, Drowned World/Substitute For Love, Beautiful Stranger, Music, Hollywood.
On December 30 1989, Dear Jessie peaked at number-five on the UK singles chart. The track was released as the fourth single from Like A Prayer in Europe (with the exception of France which instead opted to service the North American/Japanese fourth single, Oh Father) and as the fifth single in Australia.
Dear Jessie was written and produced by Madonna and Patrick Leonard and was inspired by Leonard’s young daughter, Jessie, with whom Madonna had developed a special connection.
The psychedelia-infused reflection on childhood fantasy and innocence was particularly poignant within the context of the Like A Prayer album’s sequencing, with its segue into Oh Father offering a stark musical and emotional contrast that is perhaps one of the most effective in Madonna’s body of work.
During a Twitter Q&A Madonna held on March 27, 2012, to promote her new album, deadmau5 tweeted her:
“You’re a role model to 100’s of millions. You have a powerful voice, EDM could use your positive influence, not ‘molly’ talk.”
Madonna responded by tweeting an old picture of herself wearing Mickey Mouse ears, captioned:
“From one mouse to another, I don’t support drug use and I never have. I was referring to the song called Have You Seen Molly written by my friend Cedric Gervais who I almost worked with on my album.”
“Fair enough, i was just voicing my concerns as i usually do. +1 respect for clearing it up personally.”
Watch Madonna rehearse “I’m Addicted” from the MDNA World Tour in Florence:
March 21 2014 marked the 25th Anniversary of Madonna’s Like a Prayer album. Like a Prayer was released on March 21, 1989 by Sire Records. Madonna worked with Stephen Bray, Patrick Leonard, and Prince on the album while co-writing and co-producing all the songs.
Six singles were released from the album: Like a Prayer, Express Yourself, Cherish, Oh Father, Dear Jessie, and Keep It Together.