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=== 2018–2020: ''DiCaprio 2'' ===
{{Main|DiCaprio 2}}
In June 2018, he was featured on the cover of ''[[XXL (magazine)#Annual Freshman List|XXL's 2018 Freshman Class]].<ref>{{cite web|url=http://www.xxlmag.com/news/2018/06/2018-xxl-freshman-cover/|title=XXL 2018 Freshman Class Revealed|publisher=XXL|date=June 12, 2018|access-date=June 13, 2018}}</ref>'' In July, he was featured on [[Denzel Curry]]'s "Sirens" from ''[[Ta13oo]]'', and was announced he would go on tour with [[Mac Miller]] and [[Thundercat (musician)|Thundercat]]. However, the tour was cancelled due to the passing of Mac Miller.<ref>{{Cite web | url=http://www.xxlmag.com/news/2018/07/mac-miller-swimming-tour/ | title=Mac Miller Shares the Swimming Tour Dates with Thundercat & J.I.D – XXL| date=July 23, 2018}}</ref> The first single for his second album was released on September 18, titled "[[151 Rum (song)|151 Rum]]".<ref>{{cite web |author1=JIDVevo |title=J.I.D – 151 Rum |url=https://www.youtube.com/watch?v=k_TbOH8iE4U |website=[[YouTube]] |access-date=September 19, 2018 |date=September 19, 2018}}</ref> On October 3, 2018, JID premiered the song "Working Out" on ''A COLORS SHOW''.<ref name=wo>{{cite web |last1=Findlay |first1=Mitch |title=J.I.D Sets The Jazz Bar Ablaze On "Working Out" |url=https://www.hotnewhiphop.com/jid-sets-the-jazz-bar-ablaze-on-working-out-new-song.1980540.html |website=HotNewHipHop |access-date=October 3, 2018 |date=October 3, 2018}}</ref> On his birthday, his second album ''[[DiCaprio 2]]'' was announced for a release date of November 26, 2018, and revealed the tracklist soon after.<ref>{{Cite web | url=http://www.xxlmag.com/news/2018/11/j-i-d-dicaprio-2-album-cover-release-date/ |title = J.I.D Shares 'DiCaprio 2' Album Cover and Release Date – XXL| date=November 2018 }}</ref> The album's second official single, "[[Off Deez]]" featuring [[J. Cole]], was released on November 6.<ref>{{cite web |last1=Findlay |first1=Mitch |title=J.I.D & J. Cole's Insane Collaboration "Off Deez" Drops Tomorrow |url=https://www.hotnewhiphop.com/jid-and-j-coles-insane-collaboration-off-deez-drops-tomorrow-news.63795.html |website=Hotnewhiphop|date=November 5, 2018 }}</ref> Other collaborators on the album include [[ASAP Ferg|A$AP Ferg]], [[6LACK]], [[Ella Mai]], [[BJ the Chicago Kid]], [[Method Man]] and [[Joey Badass|Joey Bada$$]], with production mainly coming from his in-house team of [[Christo (producer)|Christo]], Hollywood JB, J. Cole and [[Elite (producer)|Elite]], among others.<ref>{{cite web |last1=Centeno |first1=Tony M. |title=J.I.D Drops 'DiCaprio 2' Album Tracklist and Production Credits |url=http://www.xxlmag.com/news/2018/11/j-i-d-dicaprio-2-tracklist-album-producer-credits/ |website=XXL |date=November 12, 2018 |access-date=November 21, 2018}}</ref>
''DiCaprio 2'' was released on November 26, 2018, to positive reviews and critical acclaim.<ref>{{Cite news|url=https://www.thefader.com/2018/11/26/jid-dicaprio-2|title=J.I.D. shares DiCaprio 2|work=The FADER|access-date=November 27, 2018|language=en}}</ref><ref>{{Cite news|url=https://www.stereogum.com/2023799/j-i-d-dicaprio-2-review/franchises/album-of-the-week/|title=Album Of The Week: J.I.D 'DiCaprio 2'|date=November 27, 2018|work=Stereogum|access-date=November 27, 2018}}</ref> JID announced the first leg of his headlining Catch Me If You Can tour, which included 34 dates, beginning in January 2019.<ref>{{cite web |last1=Zidel |first1=Alex |title=J.I.D Announces Dates For "Catch Me If You Can" Tour |url=https://www.hotnewhiphop.com/jid-announces-dates-for-catch-me-if-you-can-tour-news.65997.html |website=HotNewHipHop |access-date=December 4, 2018 |date=December 4, 2018}}</ref> The supporting acts were revealed to be [[Reason (American rapper)|Reason]], Hardo, and Lou The Human. On February 9, JID's show in [[Ithaca, New York]] was shut down by the police due to a visible crack forming in the ceiling underneath the venue where the concert was held.<ref>{{Cite news|url=https://cornellsun.com/2019/02/10/video-stomping-fans-at-j-i-d-show-crack-ceiling-below-ithaca-college-venue-floor/|title=Stomping Fans at J.I.D Show Crack Ceiling Below Ithaca College Venue Floor|work=The Cornell Daily Sun|access-date=February 12, 2019|language=en}}</ref> On February 12, 2019, JID announced the second leg of his Catch Me If You Can tour. The tour did include 26 dates that started in May, and featured supporting acts [[Saba (rapper)|Saba]], [[Deante' Hitchcock]], and Mereba. <ref>{{cite web |title=J.I.D. Announces New String Of "Catch Me If You Can" Tour Dates |url=https://www.hotnewhiphop.com/jid-announces-new-string-of-catch-me-if-you-can-tour-dates-news.71784.html |website=HotNewHipHop |date=February 12, 2019 |access-date=February 12, 2019}}</ref>
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