After its release, "This Used to Be My Playground" received positive reviews from
music critics. J. Randy Taraborrelli, author of
Madonna: An Intimate Biography, called the track a "melancholic performance". Michelle Morgan, author of the book
Madonna, described it as a "beautiful ballad". Similarly, Humberto Quiroga Lavié called it one of Madonna's best ballads in his essay
Secretos y Misterios de Hombres y Mujeres. Author Rikky Rooksby wrote in his book
The Complete Guide to the Music of Madonna, that the song was appropriate for the film and its nostalgic moment towards the end, showing the characters grown up and reuniting at a museum opened for themselves and the titular league. He called it "one of Madonna's very best recordings and most expressive single". While reviewing
Something to Remember, author
Chris Wade wrote in his book
The Music of Madonna, that the song conjured up a "strangely sad, nostalgic feel, reminding ourselves of memories from yesteryear". He commended Madonna's vocals calling it as the song's "premier sound" and adding that the way "she sings and captures the melancholic melody is heartbreaking [...] it's one of her finest ever ballads."
Encyclopedia Madonnica writer and journalist
Matthew Rettenmund noted in the book that the song's rise to the top of the charts was aided by its "honest delivery and aching sense of loneliness, regret and nostalgia for friendship lost."
Larry Flick from
Billboard magazine wrote, "She offers a subtle and melancholy vocal amid a string-filled production, ably handled by collaborator
Shep Pettibone". He added it as "a mature and thoroughly satisfying effort".
Cashbox called it a "reflective ballad".
Gavin Report commented, "This change of pace for Madonna is a seamless knuckler of a slow song rich in melody and thoughtfully pitched." Matthew Jacobs from
The Huffington Post, placed it at number 32 on his list "The Definitive Ranking of Madonna Singles". He wrote: "What's surprising is that this heartfelt ballad's release was sandwiched between '
Justify My Love' and '
Erotica', which corroborates the many checkered crowns that Madonna can wear". Similarly,
AllMusic's Jose F. Promis called it "a quiet predecessor to her most notorious album
Erotica". Promis also believed that the single version of the song was worth of collecting since it was not released in CD version in the United States. Sal Cinquemani from
Slant Magazine, called it one of the singer's "soundtrack gems". Writing for the
Deseret News, Chris Hicks called the song "a lovely change-of-pace number" for Madonna. Richard LeBeau from
Medium called it "a gut-wrenching ballad that explores themes related to nostalgia, grief, and heartbreak [...] the best ballad of her career and one of the best ballads of the 90s".
Louis Virtel, from
TheBacklot.com, placed "This Used to Be My Playground" at number 52 of his list "The 100 Greatest Madonna Songs". He wrote; "The theme to Madonna’s best movie is nostalgic and sweet, and it gave her a major hit that utilized the lachrymose qualities in her voice." Mary Ann A. Bautist, from the
Philippine Daily Inquirer, called it one of the singer's "alternative tunes [...] that can be as romantic and touching as any ballad". Liz Smith, from
The Toledo Blade, called it an "exquisite ballad". On his review of the compilation
Barcelona Gold,
The Daily Gazettes Bill Rice wrote: "Madonna's plaintive single 'This Used to Be My Playground', is one medal winner".
Music Week stated that "this is Madonna at her most grown up on a thoughtful, downtempo and tender track". A negative review came from
Stylus Magazines Alfred Soto, who dismissed the song as a "slushy rewrite of
Like a Prayers 'Promise to Try'". Also negative was
Stereogums Tom Breihan, who pointed out that it lacked "the dreamy sweep of older Madonna ballads like '
Crazy For You' and '
Live to Tell'. Instead, it sounds cheap and chintzy". Breihan also deemed it "exactly the wrong song for a singer like Madonna", that should've been sung by a "grand ’90s balladeer" like
Whitney Houston or
Celine Dion. "This Used to Be My Playground" was nominated for a
Golden Globe award for
Best Original Song, but lost to "
A Whole New World" from
Aladdin. It won two accolades at the
ASCAP Awards, in the categories of Most Performed Songs from Motion Pictures and Most Performed Pop Song. == Chart performance ==