Music

Adrian Younge! He makes hip-hop inspired jazz with legends from both genres and cites Portishead as one of his most beloved inspirations.

There's also Supreme Beings of Leisure, who were lesser known contemporaries of Portishead. Lots of similarities here, but they generally explore a wider breadth of feels besides depressive longing, and their sound definitely reflects that. One of my personal all-time favorite bands, these guys. Right up there with Portishead!

Edit: Mazzy Star also comes to mind for their shared tone. More of a stripped down sound in comparison, and they lean more toward bluesy folk, alt rock, and occasionally gaze than triphop, but their lyrics should have a familiar feel to Portishead fans. They might be a bit disimilar on the surface, but they share a lot of the same spirit once you pop that hood up.

Is there a specific element or specific songs that seem to stick better than others? Or are you just looking for general electronic trip hop artists?

Sneaker Pimps might fit the bill?

Ex:Re, Agnes Odell, London Grammar, Kaleida, Annie Lennox

UNKLE Req Tricky FKA Twigs Kruder and Dorfmeister (and Kruders Peace Orchestra)

Here is a list of some songs that give me similar feelings that Portishead does. They are not exactly like Portishead, but IMHO definitely worth a try.

Massive Attack - Unfinished Sympathy, Massive Attack - Teardrop, Röyksopp & Alison Goldfrapp - Impossible, Röyksopp - Vision One, Saint Saviour - This Ain't No Hymn

Massive Attack is closer to Portishead, but they don't have female vocals on all of their songs. Röyksopp goes to a bit different direction but they have many songs with different female vocalists that might be something you like.

If you like her voice, check out The Swans and Dot Allison.

Morcheeba, Hooverphonic, maybe earlier Goldfrapp.

if you like some of the weirder stuff, check out Beak> which features Geoff Barrow of Portishead.

Moloko (and Róisín Murphy's older solo stuff)

Mazzy Star, or more specifically the tracks Hope Sandoval did with Massive Attack.

Maybe you'd like Zola Blood.

TENDER seems up your alley as well.