{{Short description|1991 single by The Simpsons}} {{Good article}} {{Use mdy dates|date=December 2025}} {{Infobox song | name = Deep, Deep Trouble | cover = Deepdeeptrouble.jpg | alt = | caption = U.S. commercial CD maxi-single | type = single | artist = The Simpsons | album = The Simpsons Sing the Blues | released = March 7, 1991 | recorded = September 1990 | studio = * The Warehouse (Philadelphia, Pennsylvania) * Lion Share (Hollywood, California) | venue = | genre = *Comedy hip hop *jazz rap *R&B *novelty *pop-rap | length = 4:28<ref name=maxisingle/> | label = Geffen | writer = * Matt Groening * DJ Jazzy Jeff | producer = * John Boylan * DJ Jazzy Jeff | prev_title = Do the Bartman | prev_year = 1990 | next_title = God Bless the Child | next_year = 1991 }}

"'''Deep, Deep Trouble'''" is a rap song from the 1990 ''Simpsons'' album ''The Simpsons Sing the Blues'', performed by the fictional character Bart Simpson (voiced by Nancy Cartwright) about his trouble-making antics. It was written by Matt Groening and DJ Jazzy Jeff and recorded in September 1990.

The song was released as the second single from the album in early 1991 and an accompanying music video (directed by Gregg Vanzo) was broadcast on television on March 7, 1991. This video has since been released on DVD as part of the 2002 boxset ''The Simpsons: The Complete Second Season''.

"Deep, Deep Trouble" charted in several countries around the world, peaking at number one in Ireland and entering the top 10 in New Zealand and the United Kingdom. Critical reception of the song was positive, with its humorous lyrics and Cartwright's performance being singled out for praise.

==Background== "Deep, Deep Trouble" appeared on the successful 1990 album ''The Simpsons Sing the Blues'' that features songs sung by the characters from the American animated television series ''The Simpsons''.<ref name=Kubasik/> It was recorded along with the rest of the album during late 1990, at which point the cast members of ''The Simpsons'' were also recording the second season of the series.<ref>{{cite news|last=Hastings|first=Deborah (Associated Press)|title='The Simpsons' sing the blues|url=https://news.google.com/newspapers?id=_P0yAAAAIBAJ&sjid=iYQDAAAAIBAJ&pg=2688,5449937&dq=the+simpsons+sing+the+blues&hl=en|access-date=July 4, 2012|newspaper=The Deseret News|date=September 28, 1990|page=D11}}</ref> The song was written by ''The Simpsons'' creator Matt Groening and DJ Jazzy Jeff,<ref name=Kubasik/> and produced by DJ Jazzy Jeff and John Boylan.<ref name=Allmusic>{{cite web|title=Deep Deep Trouble|url=http://www.allmusic.com/album/deep-deep-trouble-r18053/credits|publisher=Allmusic|access-date=September 11, 2011}}</ref> DJ Jazzy Jeff provided the drum programming, keyboards, and scratches on "Deep, Deep Trouble".<ref name=Crouse>{{cite book|last=Crouse|first=Richard|title=Big Bang, Baby: Rock Trivia|year=2000|publisher=Dundurn Press Ltd|isbn=978-0-88882-219-2|page=265|url=https://books.google.com/books?id=dYFv3ifE0f4C&q=%22Deep%2C+Deep+Trouble%22+simpsons&pg=PA265}}</ref>

The song is a rap performed by the character Bart Simpson about his trouble-making antics.<ref name=Swindell>{{cite news|last=Swindell|first=Sommer|title='Simpsons Sing' is a surprise chart topper|url=https://news.google.com/newspapers?id=arBdAAAAIBAJ&sjid=vV0NAAAAIBAJ&pg=3083,1899867&dq=deep-deep-trouble+simpsons+rap&hl=en|access-date=September 11, 2011|newspaper=Observer-Reporter|date=January 17, 1991}}</ref> Groening has described it as "the tragic story of Bart Simpson, a bad youth gone worse."<ref name=Kubasik>{{cite news|last=Kubasik|first=Ben|title=TV Spots|url=https://pqasb.pqarchiver.com/newsday/access/102585706.html?dids=102585706:102585706&FMT=ABS&FMTS=ABS:FT&type=current&date=Mar+07%2C+1991&author=By+Ben+Kubasik.+STAFF+WRITER&pub=Newsday+%28Combined+editions%29&desc=TV+SPOTS&pqatl=google|access-date=September 11, 2011|newspaper=Newsday|date=March 7, 1991|archive-date=November 7, 2012|archive-url=https://web.archive.org/web/20121107231249/http://pqasb.pqarchiver.com/newsday/access/102585706.html?dids=102585706:102585706&FMT=ABS&FMTS=ABS:FT&type=current&date=Mar+07,+1991&author=By+Ben+Kubasik.+STAFF+WRITER&pub=Newsday+(Combined+editions)&desc=TV+SPOTS&pqatl=google|url-status=dead}}</ref> ''The Simpsons'' cast member Nancy Cartwright, who voices Bart on the show, provided the character's voice in "Deep, Deep Trouble" as well.<ref name=Christensen>{{cite news|last=Christensen|first=Thor|title='Simpsons' recording is just an earful|newspaper=The Milwaukee Journal|date=December 11, 1990}}</ref> The characters Homer Simpson and Maggie Simpson are also featured, with Homer (voiced by Dan Castellaneta like on the show) ranting at Bart, and Maggie sucking on her pacifier to the beat of the song.<ref name=Johnson>{{cite news|last=Johnson|first=Peter|title=CNN's Peter Arnett has filed his last report from Baghdad for a while|newspaper=USA Today|date=March 6, 1991}}</ref>

"Deep, Deep Trouble" was released in early 1991 as the second single from ''The Simpsons Sing the Blues'' after "Do the Bartman", which also features Bart rapping.<ref name=Graham>{{cite news|last=Graham|first=Jefferson|title=Simpsons' Homer get more attention|newspaper=USA Today|date=January 31, 1991|page=3D}}</ref><ref name=Miller>{{cite web|last=Miller|first=Andrew|title=Chartbitz: Wednesday, June 1, 2005|url=http://www.scoop.co.nz/stories/CU0506/S00011.htm|publisher=Scoop|access-date=September 11, 2011|date=June 1, 2005}}</ref> That single achieved much popularity, charting highly on the singles charts in Australia, Ireland, New Zealand, Norway, and the United Kingdom,<ref name="irishcharts">{{cite web |url=http://irish-charts.com/showitem.asp?interpret=The+Simpsons&titel=Do+The+Bartman&cat=s |archive-url=https://web.archive.org/web/20120217170743/http://irish-charts.com/showitem.asp?interpret=The+Simpsons&titel=Do+The+Bartman&cat=s |url-status=dead |archive-date=February 17, 2012 |title=The Simpsons - Do The Bartman (song) |publisher= Irish-Charts.com (Hung Medien) |access-date=January 25, 2012}}</ref><ref name="n.z.chart">{{cite web |url=https://charts.nz/showitem.asp?interpret=The+Simpsons&titel=Do+The+Bartman&cat=s |title=The Simpsons - Do The Bartman (song)|publisher=charts.nz (Hung Medien) |access-date=January 25, 2012}}</ref> and eventually becoming certified gold in the latter country with 400,000 units sold.<ref name="ukcert.2">{{cite web|url=http://www.bpi.co.uk/certifiedawards/search.aspx |title=Certified Awards Search |publisher=British Phonographic Industry |access-date=July 4, 2012 |url-status=dead |archive-url=https://web.archive.org/web/20110604040853/http://www.bpi.co.uk/certifiedawards/search.aspx |archive-date=June 4, 2011 }}</ref>

==Reception== {{Quote box |quote = "Alarm was buzzin', I was snoozin',<br />Supposed to get up now, but I was refusin'<br />To let reality become an intrusion,<br />'Cause in dreamy-dream land, I was cruisin'.<br />But the buzz kept buzzin', my head kept fuzzin',<br />Gave the radio a throw, and heard an explosion.<br />(''Homer:'' D'oh!)<br />Opened up my eyes, and to my surprise,<br />There stood Homer, and his temperature rise." |source = — Sample of the song's lyrics, rapped by Bart |salign = right }} The song received a positive response from critics. Sommer Swindell of the ''Observer-Reporter'' commented that "after listening to [''The Simpsons Sing the Blues''] once, no one will forget 'Deep, Deep Trouble' [...] It would be hard not to crack a smile while listening closely to the lyrics, as they are very creative and humorous."<ref name=Swindell/> Thor Christensen of ''The Milwaukee Journal'' wrote that Bart "gets in a few good yuks" in the song,<ref name="Christensen "/> and Walt Belcher of ''The Tampa Tribune'' reported that Bart "raps out an amusing story about his misadventures while mowing the lawn".<ref name=Belcher>{{cite news|last=Belcher|first=Walt|title='The Simpsons' go on record - A new album, to be released today, taps the angst that made the animated TV series a hit|newspaper=The Tampa Tribune|date=December 4, 1990|page=1F}}</ref> ''The Orange County Register''{{'}}s Cary Darling noted that "Bart turning his life into a hip-hop autobiography on 'Deep, Deep Trouble' is an absolute joy."<ref name=Darling>{{cite news|last=Darling|first=Cary|title='Simpsons' gimmicky but good|newspaper=The Orange County Register|date=November 30, 1990}}</ref> Cartwright's rapping was praised by Tom Hopkins of the ''Dayton Daily News''.<ref name=Hopkins>{{cite news|last=Hopkins|first=Tom|title=Channel hopping|newspaper=Dayton Daily News|date=March 5, 1991|page=10B}}</ref>

Commercially, the single was not as successful as "Do the Bartman", but it still charted high in a few countries, reaching number one in Ireland, the top 10 in the UK and New Zealand, and the top 20 in Sweden.

==Music video== The music video for the single premiered on the Fox network in the United States on March 7, 1991, together with the ''Simpsons'' episode "Bart's Dog Gets an "F"{{-"}} of the series' second season.<ref name=Kubasik/> When "Do the Bartman" was released it was also accompanied by a music video, which ended up being nominated for Best Special Effects at the 1991 MTV Video Music Awards and becoming the number one music video on the American network MTV.<ref>{{cite web|url=http://www.mtv.com/ontv/vma/1991/ |archive-url=https://web.archive.org/web/20080830021804/http://www.mtv.com/ontv/vma/1991/ |url-status=dead |archive-date=August 30, 2008 |title=1991 Video Music Awards |publisher=MTV|access-date=January 25, 2012}}</ref><ref>{{cite news |title=R.E.M. leads nominations for Video Music Awards |author=Hastings, Deborah |work=The Deseret News |date=July 29, 1991 }}</ref><ref name="popmatters">{{cite web|url=http://www.popmatters.com/pm/article/the-evolution-of-the-simpsons |title=The evolution of 'The Simpsons' |author=Barney, Chuck |publisher=PopMatters|date=July 23, 2007 |access-date=January 25, 2012}}</ref> The version of the song used in the video is an edit, containing fewer lyrics than the album version.

The video for "Deep, Deep Trouble", starts with son Bart being shoved into what appears to be a jail cell by father Homer, who illustrates in flashback the things he raps about in the song in a “day in the life” manner, showing how he is forced by Homer to mow the lawn after throwing a buzzing alarm clock at his father in his sleep. When Homer tells Bart to hurry up due to his slow pace, the boy accidentally runs over the sprinkler, thus resulting in him staying home when the family goes to see a boat show. After they leave, and after Bart finishes a brief sunbathing period, he decides to throw a party and invites his friends. They make a mess in the house and when Homer and Marge return home, along with their daughters Lisa and Maggie, Bart realizes he is in, indeed, deep deep trouble. The next day, Homer later takes Bart to the barber, where his hair is shaved off, and is then laughed at by his peers because of it.<ref name="dvd"/> During each chorus until the final verse, Bart finds himself in a different punishment-type scenario. First, Bart tumbles down into a courtroom where multiple Homer clones and his witnesses find Bart guilty. Then in the next one, Bart is in a “capital punishment” situation via electric chair, before escaping the Homer officers’ cuffs, but then winds up in the chair anyway, ready to be shocked. Finally in the last scenario, Bart plummets down to Hell and is greeted by a wheel that lands on “Re-incarnation” after it has spun, but only to appear reincarnated as a snail. Joanne Ostrow of ''The Denver Post'' thought the video was not "nearly as clever as the cartoon" and that it had "'promotional gimmick' written all over it."<ref name=Ostrow/> "Then again, I never thought the video of the dance rap 'Do the Bartman' would be a ratings hit when it aired in December. So what do I know?" she added.<ref name=Ostrow>{{cite news|last=Ostrow|first=Joanne|title=Savvy 'Simpsons' slips in a plug for latest music video|newspaper=The Denver Post|date=March 6, 1991|page=1F}}</ref>

The music video features both original animation and old animation from the series and the ''Simpsons'' shorts that aired on ''The Tracey Ullman Show'' before they were spun off into ''The Simpsons'' in 1989.<ref name="dvd">''The Simpsons: The Complete Second Season'' DVD commentary for the music video "Deep, Deep Trouble".</ref> Gregg Vanzo directed the video, which, according to him, features quicker character poses than in episodes of the show to allow the animation to match the hip-hop beat.<ref name="dvd"/> The music video was later included on the 2002 DVD boxset ''The Simpsons: The Complete Second Season'', with audio commentary from its producers.<ref>{{cite news|title=Video & DVD|url=http://www.nowtoronto.com/movies/story.cfm?content=133099|access-date=September 11, 2011|newspaper=Now|date=August 8–15, 2002}}</ref><ref>{{cite web|title=The Simpsons - The Complete 2nd Season|url=http://www.tvshowsondvd.com/releases/Simpsons-Complete-2nd-Season/1107|publisher=TVShowsOnDVD.com|access-date=September 11, 2011|url-status=dead|archive-url=https://web.archive.org/web/20120806011734/http://www.tvshowsondvd.com/releases/Simpsons-Complete-2nd-Season/1107|archive-date=August 6, 2012}}</ref>

==Track listing== * '''US maxi-single CD'''<ref name=maxisingle>{{cite web|title=Deep Deep Trouble (CD&nbsp;– Geffen #21633)|url=http://www.allmusic.com/album/release/deep-deep-trouble-mr0001711174|publisher=Allmusic|access-date=July 2, 2012}}</ref> # "Deep, Deep Trouble" (Dance Mix Edit) (remixed by DJ Jazzy Jeff) &nbsp;– 4:13 # "Deep, Deep Trouble" (Full Dance Mix) (remixed by DJ Jazzy Jeff) &nbsp;– 5:50 # "Deep, Deep Trouble" (LP Version)&nbsp;– 4:28 # "Sibling Rivalry" (LP Version)&nbsp;– 4:40

==Charts== {{col-begin}} {{col-2}}

===Weekly charts=== {|class="wikitable sortable plainrowheaders" style="text-align:center" |+Weekly chart performance for "Deep, Deep Trouble" !Chart (1991) !Peak<br />position |- {{single chart|Australia|35|artist=The Simpsons feat. Bart & Homer|song=Deep, Deep Trouble|rowheader=true|access-date=March 24, 2018}} |- {{single chart|Flanders|41|artist=The Simpsons feat. Bart & Homer|song=Deep, Deep Trouble|rowheader=true|access-date=March 24, 2018}} |- !scope="row"|Europe (Eurochart Hot 100)<ref>{{cite magazine|url=https://worldradiohistory.com/UK/Music-and-Media/90s/1991/MM-1991-05-04.pdf|title=Eurochart Hot 100 Singles|magazine=Music & Media|volume=8|issue=18|page=25|date=May 4, 1991|access-date=September 18, 2020}}</ref> | 25 |- !scope="row"|Finland (Suomen virallinen lista)<ref>{{cite book|first=Jake|last=Nyman|year=2005|title=Suomi soi 4: Suuri suomalainen listakirja|edition=1st|publisher=Tammi|location=Helsinki|isbn=951-31-2503-3|language=fi}}</ref> | 15 |- {{single chart|Germany|45|artist=The Simpsons feat. Bart & Homer|song=Deep, Deep Trouble|songid=18027|rowheader=true|access-date=March 24, 2018}} |- {{single chart|Ireland2|1|song=Deep Deep Trouble|artist=The Simpsons|rowheader=true|access-date=March 24, 2018}} |- !scope="row"|Netherlands (Dutch Top 40 Tipparade)<ref>{{cite web |url=https://www.top40.nl/tipparade/1991/week-23|title=Tipparade-lijst van week 23, 1991|lang=dutch| publisher=Dutch Top 40|access-date=March 16, 2023}}</ref> | 3 |- {{single chart|Dutch100|37|artist=The Simpsons feat. Bart & Homer|song=Deep, Deep Trouble|rowheader=true|access-date=March 24, 2018}} |- {{single chart|New Zealand|10|artist=The Simpsons feat. Bart & Homer|song=Deep, Deep Trouble|rowheader=true|access-date=March 24, 2018}} |- {{single chart|Sweden|13|artist=The Simpsons feat. Bart & Homer|song=Deep, Deep Trouble|rowheader=true|access-date=March 24, 2018}} |- {{single chart|UK|7|date=19910420|rowheader=true|access-date=March 24, 2018}} |- !scope="row"|UK Airplay (''Music Week'')<ref>{{cite magazine|url=https://www.worldradiohistory.com/UK/Music-Week/1991/MW-1991-04-27.pdf|title=Playlist Chart|magazine=Music Week|date=April 27, 1991|page=18|access-date=October 15, 2025}}</ref> | 28 |- {{single chart|Billboardhot100|69|artist=The Simpsons Featuring Bart Homer|rowheader=true|access-date=March 24, 2018}} |- {{single chart|Billboardrandbhiphop|37|artist=The Simpsons Featuring Bart Homer|rowheader=true|access-date=January 31, 2026}} |- !scope="row"|US ''Cash Box'' Top 100<ref>{{cite web|url=https://www.popmusichistory.co.uk/usa-cashbox-summaries|title=USA Cashbox Charts Summaries|website=popmusichistory|access-date=December 14, 2022}}</ref> | 66 |} {{col-2}}

===Year-end charts=== {|class="wikitable plainrowheaders" style="text-align:center" |+Year-end chart performance for "Deep, Deep Trouble" !Chart (1991) !Position |- !scope="row"|Sweden (Topplistan)<ref>{{cite web|url=http://www.grammotex.se/topp91singlar.htm|title=Årstopplistan 1991, Singlar|publisher=Grammotex|language=sv|url-status=dead|archive-url=https://web.archive.org/web/20010225020647/http://www.grammotex.se/topp91singlar.htm|archive-date=February 25, 2001|access-date=April 7, 2025}}</ref> | 91 |- !scope="row"|UK Singles (OCC)<ref>{{cite magazine|title=1991 Top 100 Singles|magazine=Music Week|page=20|date=January 11, 1992}}</ref> | 97 |} {{col-end}}

==References== {{Reflist}}

{{Simpsons albums}}

{{Authority control}}

Category:1990 songs Category:1991 singles Category:American hip-hop songs Category:Animated films based on animated series Category:Animated music videos Category:Geffen Records singles Category:Irish Singles Chart number-one singles Category:The Simpsons songs Category:Songs about fictional male characters Category:Songs written by DJ Jazzy Jeff