{{Short description|American rapper}} {{distinguish|Sleepy Hollow (disambiguation){{!}}Sleepy Hollow}} {{Use American English|date=September 2021}} {{Use mdy dates|date=November 2021}} {{Infobox musical artist | name = Sleepy Hallow | image = File:Sleepy Hallow in 2019.png | caption = Sleepy Hallow in 2019 | birth_name = Tegan Chambers | birth_date = 20th December 1999 | birth_place = Jamaica | origin = Flatbush Brooklyn, New York City, U.S | genre = {{hlist|East Coast Hip hop|Brooklyn drill|emo rap|R&B}} | occupations = {{hlist|Rapper|singer|songwriter}} | years_active = 2017–present | label = {{hlist|Winners Circle|RCA<ref>{{cite web |title=Sleepy Hallow|url=https://winnerscirclestore.com/|website=rcarecords.com}}</ref>}} | website = {{URL|winnerscirclestore.com}} }}
'''Tegan Joshua Anthony Chambers''', known professionally as '''Sleepy Hallow''', is a Jamaican-American rapper and singer-songwriter who specializes in Brooklyn drill. Born in Jamaica, Chambers was raised in Flatbush, Brooklyn, New York City, alongside frequent collaborator and co-founder of Winners Circle Entertainment Sheff G.
Signing with Winners Circle Entertainment in 2019, the label entered a joint venture with RCA Records the following year. Chambers first saw recognition for his verse on the Sheff G's 2019 single, "Flow".<ref>{{Cite web|last=Reneau|first=Steven|date=August 1, 2019|title=Sheff G & Sleepy Hallow Break Down The Meaning Of "Flows"|url=https://genius.com/videos/Sheff-g-sleepy-hallow-break-down-the-meaning-of-flows|access-date=September 14, 2020|website=Genius}}</ref> His 2020 single, "Deep End Freestyle" (featuring Fousheé) received platinum certification by the Recording Industry Association of America (RIAA) and marked his first entry on the ''Billboard'' Hot 100.<ref name="riaa.com">{{Cite web|title=SLEEPY HALLOW – DEEP END FREESTYLE (FEAT. FOUSHEÉ)|url=http://www.riaa.com/gold-platinum/?share=21656&t=t|access-date=August 15, 2020|website=RIAA}}</ref> His 2021 single, "2055" peaked at number 51 on the chart.<ref>{{Cite magazine|date=August 12, 2020|title=Winner Circle Entertainment's Sleepy Hallow & Sheff G Announce Partnership With RCA Records: Exclusive|url=http://www.billboard.com/articles/news/9433088/sleepy-hallow-sheff-g-rca-records-partnership|access-date=August 15, 2020|magazine=Billboard}}</ref>
== Early life == As a child, Chambers immigrated from Jamaica to the Flatbush section of Brooklyn, New York City. Around the age of 12, he started to rap. He later picked the name "Sleepy Hallow" as his rap name as that was his name in the streets. Chambers dropped out of school in the ninth grade.<ref>{{Cite magazine|last=Lee|first=Cydney|date=2021-09-21|title=Sleepy Hallow: September's R&B/Hip-Hop Rookie of the Month|url=https://www.billboard.com/music/rb-hip-hop/sleepy-hallow-september-rb-hip-hop-rookie-9632769/|access-date=2021-11-30|magazine=Billboard|language=en-US}}</ref> He first met friend and collaborator Sheff G when the two were preparing to fight, but stopped when Sheff G was impressed with how Chambers carried himself.<ref>{{Citation|title=Sleepy Hallow & Sheff G Exclusive Interview How did they meet & more| date=November 2, 2019 |url=https://www.youtube.com/watch?v=EGcjVLwiXko|language=en|access-date=2021-11-30}}</ref>
== Career == He, Sheff G, and DizzyGotBands were signed to former NFL player Junior Galette's music record label Nula Entertainment from 2017 to 2018.<ref>{{Cite web|last=Romaker|first=Ian|date=May 4, 2018|title=Shimmy Shimmy Ya – Sheff G climbs from the New York underground|url=https://lemonwire.com/2018/05/04/shimmy-shimmy-ya-sheff-g-climbs-from-the-new-york-underground/|access-date=August 15, 2020|website=LemonWire}}</ref>
In 2019, Sleepy Hallow released his debut mixtape, ''Don't Sleep''.<ref>{{Cite web|title=Brooklyn's Sleepy Hallow Drops Off Debut Project "Don't Sleep" Ft. Sheff G|url=https://www.hotnewhiphop.com/196734-brooklyns-sleepy-hallow-drops-off-debut-project-dont-sleep-ft-sheff-g-new-mixtape|access-date=August 13, 2020|website=HotNewHipHop|date=November 2019}}</ref> In the same year, Winners Circle Entertainment was founded, with Sleepy Hallow as one of the first signees.<ref>{{Cite web|title=WINNERS CIRCLE ENTERTAINMENT ANNOUNCES PARTNERSHIP WITH RCA RECORDS SHEFF G & SLEEPY HALLOW RELEASE NEW RECORD "TIP TOE" – Sony Music Canada|url=https://www.sonymusic.ca/press_release/winners-circle-entertainment-announces-partnership-with-rca-records-sheff-g-sleepy-hallow-release-new-record-tip-toe|access-date=2021-11-30|website=www.sonymusic.ca}}</ref>
In 2020, he released his second mixtape, ''Sleepy for President''.<ref>{{Cite web|title=Sleepy Hallow: Sleepy For President|url=https://pitchfork.com/reviews/albums/sleepy-hallow-sleepy-for-president/|access-date=August 13, 2020|website=Pitchfork}}</ref><ref>{{Cite web|title=Listen to Sleepy Hallow's Project 'Sleepy for President'|url=https://www.complex.com/music/2020/06/sleepy-hallow-sleepy-for-president|access-date=August 13, 2020|website=Complex}}</ref> The mixtape featured the hit single "Deep End Freestyle" featuring Fousheé, which peaked on the U.S. ''Billboard'' Hot 100 chart at number 80 on June 20, 2020.<ref>{{Cite magazine|title=The Billboard Hot 100 Chart|url=https://www.billboard.com/charts/the-billboard-hot-100/2020-06-20|access-date=August 13, 2020|magazine=Billboard}}</ref> The single has over 85 million streams and was certified gold by RIAA in August 2020.<ref>{{Cite web|date=August 12, 2020|title=NY Drill Stars Sheff G & Sleepy Hallow Ink RCA Deal|url=https://hiphopdx.com/news/id.57299/title.ny-drill-stars-sheff-g-sleepy-hallow-ink-rca-deal|access-date=August 15, 2020|website=HipHopDX}}</ref><ref name="riaa.com" />
In August 2020, Winners Circle Entertainment started a partnership with RCA Records.<ref>{{Cite magazine|date=August 12, 2020|title=Winner Circle Entertainment's Sleepy Hallow & Sheff G Announce Partnership With RCA Records: Exclusive|url=http://www.billboard.com/articles/news/9433088/sleepy-hallow-sheff-g-rca-records-partnership|access-date=August 13, 2020|magazine=Billboard}}</ref> Sleepy Hallow and Sheff G released the single "Tip Toe", produced by Great John.<ref>{{Cite web|title=Sheff G and Sleepy Hallow Announce RCA Records Partnership, Share New Song "Tip Toe"|url=https://www.complex.com/music/2020/08/sheff-g-sleepy-hallow-rca-records-partnership-tip-toe|access-date=August 23, 2020|website=Complex}}</ref>
In June 2021, he released his first studio album, ''Still Sleep?''<ref name="Revolt">{{cite web|url=https://www.revolt.tv/platform/amp/new-music/2021/4/16/22388046/sleepy-hallow-2055-video|title=Sleepy Hallow ventures into the year "2055" in new visual|work=Revolt|last=Cho|first=Regina|date=April 16, 2021|access-date=July 16, 2021|archive-date=July 16, 2021|archive-url=https://web.archive.org/web/20210716182747/https://www.revolt.tv/platform/amp/new-music/2021/4/16/22388046/sleepy-hallow-2055-video|url-status=dead}}</ref> The album includes the single, "2055", which was released alongside a video that sees an animated Sleepy Hallow in an alternate, futuristic universe.<ref name="Revolt" /> The single would be certified double platinum in March 2022.<ref>{{Cite web|title=Gold & Platinum|url=https://www.riaa.com/gold-platinum/?tab_active=default-award&ar=Sleepy+Hallow&ti=2055&format=Single&type=#search_section|access-date=2021-11-30|website=RIAA|language=en-US}}</ref>
In September 2022, he released his single "2 Mins of Pain".<ref>{{Cite web |title=Sleepy Hallow narrates "2 Minutes of Pain" in latest single |url=https://www.revolt.tv/article/2022-09-08/190846/sleepy-hallow-2-minutes-of-pain-song/ |access-date=2022-12-04 |website=REVOLT |language=en-US}}</ref>
In November 2022, he released the single "Marie".<ref>{{cite web|url=https://www.revolt.tv/article/2022-11-02/250133/sleepy-hallow-marie-song/|title=Sleepy Hallow drops new "Marie" single|last=Cho|first=Regina|date=November 2, 2022|website=Revolt|access-date=November 3, 2022}}</ref>
In May 2023, Sleepy Hallow was charged in a 140-count indictment, as the district attorney's office said the gang is linked to 12 shootings and a murder that was caught on camera.<ref>{{Cite web |last=Santia • • |first=Marc |date=2023-05-16 |title=NYC Rappers Sheff G and Sleepy Hallow Arrested in Brooklyn Gang Bust |url=https://www.nbcnewyork.com/news/local/crime-and-courts/nyc-rappers-sheff-g-and-sleepy-hallow-arrested-in-brooklyn-gang-bust/4338346/ |access-date=2023-05-17 |website=NBC New York |language=en-US}}</ref>
On September 15, 2023, Sleepy Hallow released “Boy Meets World", his second studio album since getting out of jail. It features songs such as "GBG" featuring Marshmello and "Anxiety" featuring Doechii.{{citation needed|date=September 2023}}
On February 14, 2024, Sleepy Hallow released the single "Cupid's Guidance".<ref>{{Cite web |date=2024-02-15 |title=Sleepy Hallow Gets 'Cupid's Guidance' On New 112-Sampling Single |url=https://hiphopdx.com/news/sleepy-hallow-new-single-112-sampling-listen |access-date=2024-05-24 |website=HipHopDX |language=en}}</ref> On May 8, 2024, he released single "Winners In Paris".<ref>{{Cite web |title=SLEEPY HALLOW SHARES NEW SINGLE "WINNERS IN PARIS" |url=https://www.rcarecords.com/news/sleepy-hallow-shares-new-single-winners-in-paris/ |access-date=2024-05-24 |website=RCA Records |language=en-US}}</ref>
== Personal life == On May 15, 2023, Chambers was indicted along with 32 other alleged gang members including Sheff G for a multitude of gang conspiracy charges.<ref>{{Cite web |last=Santia • • |first=Marc |date=2023-05-16 |title=NYC Rappers Sheff G and Sleepy Hallow Arrested in Brooklyn Gang Bust |url=https://www.nbcnewyork.com/news/local/crime-and-courts/nyc-rappers-sheff-g-and-sleepy-hallow-arrested-in-brooklyn-gang-bust/4338346/ |access-date=2023-05-19 |website=NBC New York |language=en-US}}</ref>
Chambers supported the Donald Trump 2024 presidential campaign, attending a rally in the Bronx alongside Sheff G.<ref>{{Cite web |date=2024-05-24 |title=Trump appeared on stage at his Bronx rally with two rappers charged in a felony gang case |url=https://apnews.com/article/donald-trump-sheff-g-sleepy-hallow-south-bronx-4a8788eb6b07b9d561ce553b81d0347a |access-date=2025-06-14 |website=AP News |language=en}}</ref>
== Discography == === Studio albums === {| class="wikitable plainrowheaders" style="text-align:center" |+ List of studio albums, with selected chart positions, certifications and album names ! scope="col" rowspan="2"| Title ! scope="col" rowspan="2"| Album details ! scope="col" colspan="8"| Peak chart positions ! scope="col" rowspan="2"| Certifications |- ! scope="col" style="width:3em;font-size:90%;"| US<br /><ref>Peaks on the ''Billboard'' 200: * ''Still Sleep?'': {{cite magazine|url=https://www.billboard.com/charts/billboard-200/2021-10-23|title=Billboard 200: Week of October 23, 2021|magazine=Billboard|access-date=October 19, 2021}} * ''Boy Meets World'': {{cite magazine|url=https://www.billboard.com/charts/billboard-200/2023-09-30|title=Billboard 200: Week of September 30, 2023|magazine=Billboard|access-date=September 26, 2023}}</ref> ! scope="col" style="width:3em;font-size:90%;"| US<br />R&B/HH<br /><ref>Peaks on the US Top R&B/Hip-Hop Albums: {{Cite magazine|title=Top R&B/Hip-Hop Albums Chart: Week of October 23, 2021|url=https://www.billboard.com/charts/r-b-hip-hop-albums/2021-10-23|access-date=October 19, 2021|magazine=Billboard}} * ''Boy Meets World'': {{cite magazine|url=https://www.billboard.com/charts/r-b-hip-hop-albums/2023-09-30|title=Top R&B/Hip-Hop Albums Chart: Week of September 30, 2023|magazine=Billboard|access-date=September 26, 2023}}</ref> ! scope="col" style="width:3em;font-size:90%;"| US<br />Rap<br /><ref>Peaks on the US Top Rap Albums: * ''Still Sleep?'': {{Cite magazine|title=Top Rap Albums Chart: Week of October 23, 2021|url=https://www.billboard.com/charts/rap-albums/2021-10-23|access-date=October 19, 2021|magazine=Billboard}} * ''Boy Meets World'': {{cite magazine|url=https://www.billboard.com/charts/rap-albums/2023-09-30|title=Top Rap Albums Chart: Week of September 30, 2023|magazine=Billboard|access-date=September 26, 2023}}</ref> ! scope="col" style="width:3em;font-size:90%;"| AUS<br /><ref name="AUS">Peaks in Australia: * All except noted: {{cite web|url=https://australian-charts.com/showinterpret.asp?interpret=Sleepy+Hallow|title=Discography Sleepy Hallow|website=australian-charts.com|access-date=August 2, 2025}} * ''Still Sleep?'': {{cite magazine|title=The ARIA Report: Week Commencing 30 August 2021|magazine=The ARIA Report|publisher=Australian Recording Industry Association|issue=1643|page=6|date=August 30, 2021}}</ref> ! scope="col" style="width:3em;font-size:90%;"| CAN<br /><ref>{{cite magazine|url=https://www.billboard.com/charts/canadian-albums/2021-08-28|title=Billboard Canadian Albums: Week of August 28, 2021|magazine=Billboard|access-date=August 24, 2021}} * ''Boy Meets World'': {{cite magazine|url=https://www.billboard.com/charts/canadian-albums/2023-09-30|title=Billboard Canadian Albums: Week of September 30, 2023|magazine=Billboard|access-date=September 26, 2023}}</ref> ! scope="col" style="width:3em;font-size:90%;"| DEN<br /><ref>{{cite web|url=http://hitlisten.nu/default.asp?w=34&y=2021&list=a40|title=Album Top-40 Uge 34, 2021|publisher=Hitlisten|access-date=September 1, 2021}}</ref> ! scope="col" style="width:3em;font-size:90%;"| NZ<br /><ref name="NZ">{{cite web|url=https://charts.nz/showinterpret.asp?interpret=Sleepy+Hallow|title=Discography Sleepy Hallow|website=charts.nz|access-date=August 2, 2025}}</ref> ! sope="col" style="width:3em;font-size:90%;"| SWE<br /><ref name="SWE">{{cite web|url=https://swedishcharts.com/showinterpret.asp?interpret=Sleepy+Hallow|title=Discography Sleepy Hallow|website=swedishcharts.com|access-date=August 2, 2025}}</ref> |- ! scope="row"| ''Still Sleep?'' | * Released: June 2, 2021 * Label: Winners Circle, RCA * Format: Digital download, streaming | 16 || 10 || 9 || 90 || 15 || 38 || 39 || 50 | * RIAA: Gold<ref name="RIAA">{{cite certification|region=United States|artist=Sleepy Hallow|access-date=February 10, 2023}}</ref> * BPI: Silver<ref name="BPI">{{cite certification|region=United Kingdom|artist=Sleepy Hallow|access-date=June 2, 2024}}</ref> * MC: Gold<ref name="MC">{{cite certification|region=Canada|artist=Sleepy Hallow|access-date=December 21, 2023}}</ref> * RMNZ: Gold<ref name="RMNZalbums">{{cite certification|region=New Zealand|artist=Sleepy Hallow|type=album|access-date=December 28, 2024|source=radioscope}}</ref> |- ! scope="row"| ''Boy Meets World'' | * Released: September 15, 2023 * Label: Winners Circle, RCA * Format: Digital download, streaming | 17 || 4 || 3 || 32 || 10 || — || 19 || — | |- ! scope="row"| ''Read This When You Wake Up'' | * Released: December 13, 2024<ref>{{cite web|url=https://www.rcarecords.com/news/sleepy-hallow-returns-with-new-album-read-this-when-you-wake-up/|title=RCA Records: Sleepy Hallow Returns With New Album|publisher=RCA Records|access-date=December 20, 2024}}</ref> * Label: Winners Circle, RCA * Format: Digital download, streaming | — || — || — || — || — || — || — || — | |- | colspan="12" style="font-size:90%" | "—" denotes a recording that did not chart or was not released in that territory. |}
=== Mixtapes === {| class="wikitable plainrowheaders" style="text-align:center" |+ ! scope="col" rowspan="2" | Title ! scope="col" rowspan="2" | Mixtape details ! scope="col" colspan="4" | Peak chart positions |- ! scope="col" style="width:3em;font-size:90%;"| US<br /><ref>{{Cite magazine|title=Billboard 200 Chart: Week of June 19, 2020|url=https://www.billboard.com/charts/billboard-200/2020-06-19|access-date=June 14, 2021|magazine=Billboard}}</ref> ! scope="col" style="width:3em;font-size:90%;"| US<br />R&B/HH<br /><ref>{{Cite magazine|title=Top R&B/Hip-Hop Albums Chart: Week of June 20, 2020|url=https://www.billboard.com/charts/r-b-hip-hop-albums/2020-06-20|access-date=June 15, 2021|magazine=Billboard}}</ref> ! scope="col" style="width:3em;font-size:90%;"| US<br />Rap<br /><ref>{{Cite magazine|title=Top Rap Albums Chart: Week of June 20, 2020|url=https://www.billboard.com/charts/rap-albums/2020-06-20|access-date=June 15, 2021|magazine=Billboard}}</ref> ! scope="col" style="width:3em;font-size:90%;"| CAN<br /><ref>{{Cite magazine|title=Canadian Albums Chart: Week of June 20, 2020|url=https://www.billboard.com/charts/canadian-albums/2020-06-20|access-date=June 15, 2021|magazine=Billboard}}</ref> |- ! scope="row" | ''Sleepy Hallow Presents: Sleepy for President''<ref name=":0">{{Cite web |date=May 26, 2021 |title=Sleepy Hallow Announces Debut Album, Shares New "Chicken/Mi No Sabe" Video: Watch |url=https://pitchfork.com/news/sleepy-hallow-announces-debut-album-shares-new-chicken-mi-no-sabe-video-watch/ |access-date=June 14, 2021 |website=Pitchfork}}</ref> | * Released: June 5, 2020 * Label: Winners Circle, Empire * Format: Digital download, streaming | 48 | 32 | 25 | 61 |}
=== Singles === ====As lead artist==== {| class="wikitable plainrowheaders" style="text-align:center;" |+ List of singles, with selected chart positions, showing year released and album name ! scope="col" rowspan="2" | Title ! scope="col" rowspan="2" | Year ! scope="col" colspan="8" | Peak chart positions ! scope-"col" rowspan="2" | Certifications ! scope="col" rowspan="2" | Album |- ! scope="col" style="width:3em;font-size:90%;"| US<br /><ref>Peak positions on the Hot 100: * "Deep End Freestyle": {{cite magazine|url=https://www.billboard.com/charts/hot-100/2020-06-20|title=Hot 100 Chart: Week of June 20, 2020|magazine=Billboard|accessdate=July 27, 2021}} * "2055": {{cite magazine|url=https://www.billboard.com/charts/hot-100/2021-08-28|title=Hot 100 Chart: Week of August 28, 2021|magazine=Billboard|access-date=August 24, 2021}} * "Die Young": {{cite tweet|user=billboardcharts|number=1533892128706789378|title=@SleepyHallow83's "Die Young," featuring @347Aidan, debuts at No. 60 on this week's #Hot100.|date=June 6, 2022|access-date=June 7, 2022}} * "Anxiety": {{cite tweet|user=billboardcharts|number=1899152373332758787|title=@SleepyHallow83's "A N X I E T Y" featuring @justdoechii debuts at No. 45 on this week's #Hot100.|date=March 10, 2025|access-date=March 11, 2025}}</ref> ! scope="col" style="width:3em;font-size:90%;"| AUS<br /><ref name="AUS"/> ! scope="col" style="width:3em;font-size:90%;"| CAN<br /><ref>Peak positions on the Canadian Hot 100: * "Deep End Freestyle": {{cite magazine|url=https://www.billboard.com/charts/canadian-hot-100/2020-06-20|title=Canadian Hot 100 Chart: Week of June 20, 2020|magazine=Billboard|access-date=July 27, 2021}} * "2055": {{cite magazine|url=https://www.billboard.com/charts/canadian-hot-100/2021-08-21|title=Canadian Hot 100 Chart: Week of August 21, 2021|magazine=Billboard|access-date=August 17, 2021}} * "Die Young": {{cite magazine|url=https://www.billboard.com/charts/canadian-hot-100/2022-06-11|title=Canadian Hot 100 Chart: Week of June 11, 2022|magazine=Billboard|access-date=June 7, 2022}} * "Anxiety": {{cite magazine|url=https://www.billboard.com/charts/canadian-hot-100/2025-03-15|title=Canadian Hot 100 Chart: Week of March 15, 2025|magazine=Billboard|access-date=March 12, 2025}}</ref> ! scope="col" style="width:3em;font-size:90%;"| IRE<br /><ref>{{cite web|url=http://irish-charts.com/showinterpret.asp?interpret=Sleepy+Hallow|archive-url=https://web.archive.org/web/20221111233944/http://irish-charts.com/showinterpret.asp?interpret=Sleepy+Hallow|url-status=dead|archive-date=November 11, 2022|title=Discography Sleepy Hallow|website=irish-charts.com|access-date=November 12, 2022}}</ref> ! scope="col" style="width:3em;font-size:90%;"| NZ<br /><ref name="NZ"/> ! scope="col" style="width:3em;font-size:90%;"| SWE<br /><ref name="SWE"/> ! scope="col" style="width:3em;font-size:90%;"| UK<br /><ref>{{Cite web|title=SLEEPY HALLOW & FOUSHEE {{!}} full Official Chart History|url=https://www.officialcharts.com/artist/57851/sleepy-hallow-and-foushee/|access-date=June 15, 2021|website=Official Charts Company}}</ref> ! scope="col" style="width:3em;font-size:90%;"| WW<br /><ref>{{cite magazine|url=https://www.billboard.com/artist/doechii/chart-history/glo/|title=Doechii Chart History: ''Billboard'' Global 200|magazine=Billboard|access-date=March 11, 2025}}</ref> |- ! scope="row"| "Deep End Freestyle"<br />{{small|(with Fousheé)}} | rowspan="5" | 2020 | 80 || — || 69 || — || — || — || 93 || — | * RIAA: Platinum<ref name="RIAA"/> * BPI: Silver<ref name="BPI"/> * RMNZ: Gold<ref name="RMNZsingles">{{cite certification|region=New Zealand|type=single|artist=Sleepy Hallow|access-date=February 11, 2026|source=radioscope}}</ref> | rowspan="4"| ''Sleepy Hallow Presents: Sleepy for President'' |- ! scope="row"| "Don't Panic" | — || — || — || — || — || — || — || — | |- ! scope="row"| "Baddie Betty Boop" | — || — || — || — || — || — || — || — | |- ! scope="row"| "Anxiety Freestyle" | — || — || — || — || — || — || — || — | |- ! scope="row"| "Tip Toe"<br />{{small|(with Sheff G)}} | — || — || — || — || — || — || — || — | * RIAA: Gold<ref name="RIAA"/> | rowspan="2" | ''Still Sleep?'' |- ! scope="row"| "2055"<br />{{small|(solo or remix featuring Coi Leray)}}<ref name="Revolt" /> | 2021 | 51 || 13 || 17 || 21 || 11 || 65 || 21 || — | * RIAA: 4× Platinum<ref name="RIAA"/> * ARIA: 2× Platinum<ref name=ARIA2021>{{cite certification|region=Australia|certyear=2022|access-date=April 4, 2022}}</ref> * BPI: Platinum<ref name="BPI"/> * MC: 4× Platinum<ref name="MC"/> * RMNZ: 3× Platinum <ref name="RMNZsingles"/> |- ! scope="row"| "Die Young"<ref>{{cite web|url=https://www.revolt.tv/article/2022-05-26/170956/sleepy-hallow-die-young-song/|title=Sleepy Hallow gets introspective in new "Die Young" single|work=Revolt|last=Cho|first=Regina|date=May 26, 2022|access-date=May 26, 2022}}</ref><br />{{small|(featuring 347aidan)}} | rowspan="3"| 2022 | 60 || 38 || 15 || — || —{{efn|group=upper-alpha|"Die Young" did not enter the NZ Top 40 Singles Chart, but peaked at number five on the NZ Hot Singles Chart.<ref>{{cite web|url=https://aotearoamusiccharts.co.nz/archive/hot-singles/2022-06-03|title=NZ Hot Singles Chart|publisher=Recorded Music NZ|date=June 6, 2022|access-date=June 4, 2022}}</ref>}} || —{{efn|group=upper-alpha|"Die Young" did not enter the Swedish Singellista Chart, but peaked at number 17 on the Swedish Heatseeker Chart.<ref>{{cite web|url=https://www.sverigetopplistan.se/chart/215?dspy=2022&dspp=22|title=Veckolista Heatseeker, vecka 22|publisher=Sverigetopplistan|access-date=June 3, 2022}}</ref>}} || 45 || — | * RIAA: Platinum<ref name="RIAA" /> * BPI: Silver<ref name="BPI"/> * MC: Platinum<ref name="MC"/> * RMNZ: Gold<ref name="RMNZsingles"/> | ''Boy Meets World'' |- ! scope="row"| "2 Mins of Pain"<br />{{small|(featuring Alborosie)}} | — || — || — || — || —{{efn|group=upper-alpha|"2 Mins of Pain" did not enter the NZ Top 40 Singles Chart, but peaked at number 36 on the NZ Hot Singles Chart.<ref>{{cite web|url=https://aotearoamusiccharts.co.nz/archive/hot-singles/2022-09-16|title=NZ Hot Singles Chart|publisher=Recorded Music NZ|date=September 19, 2022|access-date=September 17, 2022}}</ref>}} || — || — || — | | rowspan="2" {{Non-album singles}} |- !scope="row"| "Marie" | — || — || — || — || —{{efn|group=upper-alpha|"Marie" did not enter the NZ Top 40 Singles Chart, but peaked at number 16 on the NZ Hot Singles Chart.<ref>{{cite web|url=https://aotearoamusiccharts.co.nz/archive/hot-singles/2022-11-11|title=NZ Hot Singles Chart|publisher=Recorded Music NZ|date=November 14, 2022|access-date=November 12, 2022}}</ref>}} || — || — || — | |- !scope="row"| "Pain Talk"<br />{{small|(featuring Lil Tjay)}} | rowspan="4"| 2023 | — || — || — || — || —{{efn|group=upper-alpha|"Pain Talk" did not enter the NZ Top 40 Singles Chart, but peaked at number 24 on the NZ Hot Singles Chart.<ref>{{cite web|url=https://aotearoamusiccharts.co.nz/archive/hot-singles/2023-06-02|title=NZ Hot Singles Chart|publisher=Recorded Music NZ|date=June 5, 2023|access-date=June 3, 2023}}</ref>}} || — || — || — | | rowspan="4"| ''Boy Meets World'' |- !scope="row"| "Good Girls Ain't No Fun" | — || — || — || — || —{{efn|group=upper-alpha|"Good Girls Ain't No Fun" did not enter the NZ Top 40 Singles Chart, but peaked at number 32 on the NZ Hot Singles Chart.<ref name="NZ Hot September 25">{{cite web|url=https://aotearoamusiccharts.co.nz/archive/hot-singles/2023-09-22|title=NZ Hot Singles Chart|publisher=Recorded Music NZ|date=September 25, 2023|access-date=September 23, 2023}}</ref>}} || — || — || — | |- !scope="row"| "GBG"<br />{{small|(featuring Marshmello)}} | — || — || — || — || —{{efn|group=upper-alpha|"GBG" did not enter the NZ Top 40 Singles Chart, but peaked at number 25 on the NZ Hot Singles Chart.<ref>{{cite web|url=https://aotearoamusiccharts.co.nz/archive/hot-singles/2023-09-15|title=NZ Hot Singles Chart|publisher=Recorded Music NZ|date=August 21, 2023|access-date=August 19, 2023}}</ref>}} || — || — || — | |- !scope="row"| "Anxiety"<br />{{small|(featuring Doechii)}} | 45 || 14 || 25 || 12 || 5 || 28 || 15 || 21 | * RIAA: Gold<ref name="RIAA"/> * MC: Platinum<ref name="MC"/> * RMNZ: Platinum<ref name="RMNZsingles"/> |- !scope="row"| "Winners in Paris" | 2024 | — || — || — || — || —{{efn|group=upper-alpha|"Winners in Paris" did not enter the NZ Top 40 Singles Chart, but peaked at number 36 on the NZ Hot Singles Chart.<ref>{{cite web|url=https://aotearoamusiccharts.co.nz/archive/hot-singles/2024-05-17|title=NZ Hot Singles Chart|publisher=Recorded Music NZ|date=May 20, 2024|access-date=May 17, 2024}}</ref>}} || — || — || — | | ''Read This When You Wake Up'' |- !scope="row"| "Calm 3" | 2025 | — || — || — || — || —{{efn|group=upper-alpha|"Calm 3" did not enter the NZ Top 40 Singles Chart, but peaked at number 37 on the NZ Hot Singles Chart.<ref>{{cite web|url=https://aotearoamusiccharts.co.nz/archive/hot-singles/2025-08-01|title=NZ Hot Singles Chart|publisher=Recorded Music NZ|date=August 1, 2025|access-date=August 2, 2025}}</ref>}} || — || — || — | | {{Non-album single}} |- | colspan="12" style="font-size:90%" | "—" denotes a recording that did not chart or was not released in that territory. |}
==== As featured artist ==== {| class="wikitable plainrowheaders" style="text-align:center;" |+ List of singles as a featured artist, showing year released and album name ! scope="col" style="width:19em;" | Title ! scope="col" | Year ! scope="col" | Album |- ! scope="row"| "Panic"<br />{{small|(Sheff G featuring Sleepy Hallow and Double G)}} | rowspan="2"| 2017 | rowspan="2" {{Non-album singles}} |- ! scope="row"| "Hurtin{{'-}}"<br />{{small|(Sheff G featuring Sleepy Hallow)}} |- ! scope="row"| "Automatic"<br />{{small|(Sheff G featuring Sleepy Hallow)}} |rowspan="4"| 2018 |''The Unluccy Luccy Kid'' |- ! scope="row"| "Addicted to the Cash"<br />{{small|(Sheff G featuring Sleepy Hallow)}} |rowspan="3" {{n/a|Non-album singles}} |- ! scope="row"| "Panic 2"<br />{{small|(Sheff G featuring Sleepy Hallow)}} |- ! scope="row"| "Panic 3"<br />{{small|(Sheff G featuring Sleepy Hallow)}} |- ! scope="row"| "Flows, Pt.2"<br />{{small|(Sheff G featuring Sleepy Hallow)}} |rowspan="2"| 2019 |''The Unluccy Luccy Kid'' |- ! scope="row" | "Brazy"<br />{{small|(J.I the Prince of N.Y featuring Sleepy Hallow)}} |{{n/a|Non-album single}} |- ! scope="row" | "Make It Happen"<br />{{small|(Sheff G featuring Sleepy Hallow)}} | rowspan="2" | 2020 |''Just 4 Yall'' |- ! scope="row"| "Goat Freestyle"<br />{{small|(Eli Fross featuring Sleepy Hallow)}} |''Cesar'' |- ! scope="row" | "Run It Up"<br />{{small|(Sheff G featuring Sleepy Hallow and A Boogie wit da Hoodie)}} | rowspan="1" | 2021 | ''From The Can'' |- ! scope="row" | "No Love"<br />{{small|(Fredo Bang featuring Sleepy Hallow)}} | rowspan="2" | 2022 |''Two-Face Bang 2'' |- !scope="row"| "Bad Days"<br />{{small|(Eli Fross featuring Sleepy Hallow)}} | ''The Golden Child'' |}
=== Other charted and certified songs === {| class="wikitable plainrowheaders" style="text-align:center" |+ ! rowspan="2" |Title ! rowspan="2" |Year !Peak chart positions ! rowspan="2" |Certifications ! rowspan="2" |Album |- ! scope="col" style="width:3em;font-size:90%;"| NZ<br />Hot<br /><ref name="NZ Hot September 25"/> |- ! scope="row"| "Breakin Bad (Okay)"<br />{{small|(featuring Sheff G)}} | 2019 | — | * RIAA: Gold<ref name=RIAA/> | ''Don't Sleep'' |- ! scope="row"| "Molly"<br />{{small|(featuring Sheff G)}} | rowspan=2 | 2020 | — | * RIAA: Platinum<ref name="RIAA"/> * RMNZ: Gold<ref name="RMNZsingles"/> | ''Sleepy Hallow Presents: Sleepy For President'' |- ! scope="row"| "Weight On Me"<br />{{small|(with Sheff G)}} | — | * RIAA: Gold<ref name="RIAA"/> * RMNZ: Gold<ref name="RMNZ"/> | ''One and Only'' |- ! scope="row"|"Basketball Dreams (Intro)" | |— | * RIAA: Gold<ref name="RIAA" /> | rowspan="4" |''Still Sleep?'' |- ! scope="row" | "Scrub" | rowspan="3" |2021 |39<br /><ref>{{Cite web|title=Hot Singles Chart|url=https://aotearoamusiccharts.co.nz/archive/hot-singles/2018-07-27|access-date=June 14, 2021|website=The Official New Zealand Music Chart}}</ref> | |- ! scope="row"|"1999" |— | * RIAA: Gold<ref name="RIAA" /> |- ! scope="row"|"Lowkey" |— | * RIAA: Gold<ref name="RIAA" /> |- ! scope="row"|"Driver's Seat (Intro)" | rowspan="2"| 2023 |25 | | rowspan="2"| ''Boy Meets World'' |- ! scope="row"|"All the Way" |33 | |- | colspan="11" style="font-size:90%" | "—" denotes a recording that did not chart or was not released in that territory. |}
===Guest appearances=== {| class="wikitable plainrowheaders" style="text-align:center;" |+ List of non-single guest appearances, with other performing artists, showing year released, certifications and album name ! scope="col" | Title ! scope="col" | Year ! scope="col" | Other artist(s) ! scope="col" | Certifications ! scope="col" | Album |- !scope="row" | "Flows" | 2019 | Sheff G | * RMNZ: Gold<ref name="RMNZsingles"/> | ''The Unluccy Luccy Kid'' |- !scope="row" | "Demon Flow" | rowspan="5"| 2020 | Yak Yola, Sheff G | | ''Misunderstood'' |- !scope="row" | "Wet Em Up Pt.2" | Lil Tjay, Sheff G | | ''State of Emergency'' |- !scope="row" | "Lil Big Bro Shit" | Sheff G | | ''One and Only'' |- !scope="row" | "Head Tap" | Pressa, Sheff G | | ''Gardner'' |- !scope="row" | "Goat Freestyle" | Eli Fross | | ''Cesar'' |- !scope="row" | "2020 Vision" | rowspan="3"| 2021 | DJ Drewski, Sheff G | | ''Seat at the Table'' |- !scope="row" | "Steppas Freestyle" | Eli Fross | | ''The Book of Eli'' |- !scope="row" | "Run Up" |Hamo Crime, mauley G, Sheff G, Rah Swish | |''Year of the H 3'' |- !scope="row" | "Like Me" | rowspan="3"| 2022 | rowspan="2"| Sheff G | | rowspan="3"| ''From The Can'' |- !scope="row" | "Bad Breed" | |- !scope="row" | "Overseas" | Jay Bezzy, Sheff G | |}
== Notes == {{notelist-ua}}
== References == {{reflist}}
== External links == * {{IMDb name}}
{{Authority control}}
{{DEFAULTSORT:Hallow, Sleepy}} Category:1999 births Category:Living people Category:21st-century African-American rappers Category:21st-century American rappers Category:East Coast hip-hop musicians Category:Rappers from Brooklyn Category:21st-century Jamaican male singers Category:21st-century African-American male rappers Category:21st-century American male rappers Category:African-American songwriters Category:American male songwriters Category:Jamaican emigrants to the United States Category:Jamaican male rappers Category:Jamaican male songwriters Category:Gangsta rappers Category:American drill musicians Category:American trap musicians Category:Songwriters from New York (state) Category:Crips Category:Brooklyn drill musicians