Smiley released his new single smiley tripping his cousin, featuring Casper TNG, on October 23, 2026 through OVO Sound.
The Toronto rapper, born Alexander Eli Morand, keeps his 2026 run moving with a standalone single that puts two Canadian voices on the same record. The official audio is live now on YouTube, and the single is streaming through his official smartlink. For listeners who have followed Smiley from the early OVO co-signs into a catalogue of his own, this release lands as a confident next step rather than a one off moment.
Smiley Tripping His Cousin Pairs Smiley With Casper TNG
At the centre of the record is the pairing itself. Smiley and Casper TNG trade space on a track built for Toronto rap fans, and early coverage has pointed to the chemistry between the two artists. HotNewHipHop, which covered the single on its release, described the song as a strong showcase of Toronto rap and noted that both artists sound comfortable sharing the record.
That matters because a feature only works when it adds something the lead artist could not deliver alone. Here, Casper TNG is credited as the featured artist, and the record is presented as a collaboration, not a solo track with a name attached at the end. Smiley stays the story, while the feature widens the reach of the single to another Toronto audience that already knows Casper TNG by name.
Listen through the official channels to support the release directly. The official audio is on YouTube at Smiley – Tripping His Cousin (feat. Casper TNG) [Official Audio], and the full streaming release is collected at the official link: ovo-smiley.ffm.to/trippinghiscousin. You can also follow Smiley on Instagram at @smiley61st, on YouTube at @smileybuyorbye, and on Spotify as an OVO Sound artist.
Where The Single Lands In Smiley’s 2025 And 2026 Run
This single does not arrive in isolation. It follows a steady run that has kept Smiley visible across two calendar years. In 2026 alone, it arrives after 10 Raccoons on August 21, 2026 and Two Tone on July 2, 2026, and earlier in the year after the Heartless EP with Baka Not Nice on January 16, 2026.
Before that run, Smiley closed 2025 with Never Box Me In on November 7, 2025, a project Sony Music Canada presented as Smiley in a confident era. That followed Don’t Box Me In on June 13, 2025, the album that included 2 Mazza featuring Drake. Read in order, the timeline shows an artist who has stayed active on singles, EPs and albums instead of disappearing between major moments.
That consistency is part of the story here. A standalone single in late October keeps new music in front of listeners while the earlier 2026 releases are still recent. It also gives playlists, DJs and fans a fresh entry point into the catalogue, whether they start with this track and work backwards to Two Tone and 10 Raccoons, or start with Don’t Box Me In and move forward.
The OVO Sound And Toronto Angle
Smiley’s home base has always been part of his identity. He is a Toronto rapper on OVO Sound, and his music is covered as Toronto music first. That local grounding is why a collaboration with another Canadian artist reads differently from a random feature booking. Both names carry recognition in the same city, and the single speaks to an audience that understands that context without needing it explained.
At the same time, the OVO connection gives the release a wider frame. OVO Sound releases travel beyond Toronto through the label’s global audience, and Smiley’s Spotify and social following reflect that reach. The balance is the point: a Toronto record, made by Toronto artists, that can still be discovered by hip hop listeners far outside Canada through official streaming and video platforms.
For Canadian hip hop coverage, that balance matters. Major Canadian releases deserve the same clear, dated and sourced treatment as any other major release, with the official audio embedded, the official streaming link in the story, and the release date stated plainly. This post follows that standard, and it keeps the focus where Smiley has put it, on the music itself.
Smiley Drops Tripping His Cousin Single as a late October statement, and the next question is simply what follows it. With a run that already includes an EP with Baka Not Nice, two summer singles and now this Casper TNG collaboration in a single year, Smiley has built real momentum heading into the end of 2026. Stream the official audio above, run the single through the official smartlink, and keep an eye on @smiley61st for whatever he announces next.
