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.
Might also try Zero 7. Their earlier albums feature vocals from Sia and Sophie Barker, as well as José González. All three have smooth evocative voices.
Sia: Destiny, This Fine Social Scene, The Pageant of the Bizarre, Speed Dial No. 2
Sophie Barker: Spinning, Passing By, In the Waiting Line, In Time
José González: Futures, Left Behind, Today, Crosses
These were all among my favorite songs almost two decades ago, when Trip Hop was at its height. Some I would still consider to be pinnacles of music.
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?
If you like her voice, check out The Swans and Dot Allison.
Morcheeba, Hooverphonic, maybe earlier Goldfrapp.
Assume for a second that I listen to it not because it is trip hop, but because of Beth Gibbons’ vocals. Would you change that recommendation?
If you’re in the mood for something not trip hop but with a similar vocal style you might enjoy Lamb - later stuff is probably most similar, earlier stuff is a bit more esoteric.
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.
