Thank you to Gila. Definitions are underlined in the clues.
Across
1. Rolling Stone review initially delighted musician (6,6)
STEVIE WONDER : Anagram of(Rolling) [STONE REVIEW + 1st letter of(initially) “delighted“].
When he was Little …

8. Contest featuring Oxford University is level (4,3)
EVEN OUT : EVENT(a sporting contest) containing(featuring) OU(abbrev. for Oxford University).
Defn: …, as a verb.
9. Soldier possibly joins wife before heading back for port (7)
ANTWERP : ANT(a social insect, possibly a member of the soldier caste) plus(joins) W(abbrev. for “wife”) + reversal of(…. heading back) PRE-(prefix signifying something earlier in time/before).
Defn: … in Belgium.
11. Silicate almost cracks, showing signs of stress (7)
ITALICS : Anagram of(… cracks) [“Silicate” minus its last letter(almost)].
Defn: …/emphasis in text.
12. Shut your mouth after admitting lies regularly (7)
SILENCE! : SINCE(the time period after, as in “since the accident, …”) containing(admitting) 1st and 3rd letters of(… regularly) “lies“.
Defn: …!
13. Incite, say, unlimited agony (3,2)
EGG ON : EG(abbrev. for “exempli gratia”/for example/say) + “agony” minus its 1st and last letters(unlimited …).
14. Animal‘s limb badly beset by trouble (9)
ARMADILLO : ARM(a limb/a member of a body) + [ILL(badly, as in “please don’t think ill of me”) contained in(beset by) ADO(trouble/fuss).
Not the giant armadillo:

16. Leading a bike race – chortle – by 50 minutes! (2,3,4)
AT THE HELM : A + TT(abbrev. for the “Tourist Trophy” motorcycle/bike races held in the Isle of Man) + [HE HE](representing laughter/chortle) + L(Roman numeral for 50) + M(abbrev. for “minutes” in time notation).
19. Nothing featured in new online talks is well-known (5)
NOTED : O(letter representing 0/nothing) contained in(featured in) [N(abbrev. for “new”) + TED(series of talks posted online by media organisation TED Conferences LLC)].
21. Criminal thus called the shots and carried out scams (7)
HUSTLED : Anagram of(Criminal) THUS + LED(called the shots/took the lead).
23. Endlessly travelled around, having left part of Wales (7)
NEWPORT : Reversal of(… around) “wend”(travelled in a specified direction, slowly or by an indirect route) minus its last letter(Endlessly …) plus(having) PORT(the left side of a craft when facing the bow).
24. Plan 24 hours in Ibiza? Good stuff! (7)
DIAGRAM : DIA(Spanish, as spoken in Ibiza, for “day”/a 24 hour period) + G(abbrev. for “good”) + RAM(to stuff/to fill by forcing into place).
25. Cookie containing odd bits of grain and herb (7)
OREGANO : OREO(trademark name for a chocolate biscuit/cookie) containing(containing) 1st, 3rd and 5th letters of(odd bits of) “grain“.

26. Unite extremists to do what’s necessary financially (4,4,4)
MAKE ENDS MEET : [MAKE ENDS MEET](to unite/to bring together extremists/the most extreme parts).
Down
1. The terms of this fresh scheme absolutely matter! (7)
SHEBANG : Last letters, respectively, of(The terms of/the limits of, in archaic language) “this fresh scheme” + BANG(absolutely/completely, as in “bang on target”).
Defn: …/business or operation, as in “he took it upon himself to run the whole shebang”.
2. Feeling of ecstasy comes with travelling (7)
EMOTION : E(abbrev. for “ecstasy”, the drug) plus(comes with) MOTION(travelling/movement).
3. Digger finally departs from highway, leaving nothing behind (9)
INTESTATE : Last letter of(… finally) “Digger” deleted from(departs from) “interstate”(one of the system of highways/motorways running between US states).
But, the answer means to die without leaving a valid will. You can leave a lot behind but still be intestate.
4. Garments in wide, upright box (5)
WRAPS : W(abbrev. for “wide”/a delivery that is too wide, in cricket scores) + reversal of(upright, in a down clue) SPAR(to box/exchange blows without much force, as practice).
5. Wound up line that has caught on the outside (7)
NETTLED : L(abbrev. for “line”) contained in(that has … on the outside) NETTED(caught, with a net of course).
Defn: …/annoyed or irritated.
6. Persistent bird tucked into decapitated mammal (7)
ETERNAL : TERN(a seabird related to the gull) contained in(tucked into) “seal”(an aquatic mammal) minus its 1st letter(decapitated …).
Defn: …/seeming to last forever.
7. Type of property developed this decade to incorporate space (4-8)
SEMI-DETACHED : Anagram of(developed) THIS DECADE containing(to incorporate) EM(a unit of measurement of space/width in printed matter).
2 in 1:

10. Up-front requirement: change old pic on Tinder (12)
PRECONDITION : Anagram of(change) [O(abbrev. for “old”) + PIC ON TINDER].
15. Significant American in pursuit of second Oscar (9)
MOMENTOUS : US(abbrev. for things American) placed below(in pursuit of/going after, in a down clue) [MOMENT(a second/a very short period of time) + O(letter represented by “Oscar” in the phonetic alphabet)].
17. Hot jalapeño peppers to finish with … et voilà, Mexican food! (7)
TOSTADA : Last letters, respectively, of(… to finish) “Hot jalapeño peppers” plus(with) TADA!(exclamation in imitation of fanfare when presenting or announcing something dramatic/et voila!/there we are!).
18. Expatiate and agree to differ about the origins of natural law (7)
ENLARGE : Anagram of(… to differ) AGREE containing(about) 1st letters, respectively, of(the origins of) “natural law“.
Defn: …/to provide more of/expand on the details.
19. Straight away, this place is out of contention (7)
NOWHERE : NOW(straight away/immediately) + HERE(this place/where one is presently).
Defn: …/with no chance of winning in a contest.
20. Tate’s opening week has Bridget Riley works in more than one section (3-4)
TWO-PART : 1st letter of(…’s opening) “Tate” + W(abbrev. for “week” + OP ART(short for “optical art”, as represented by the works of Bridget Riley, English painter).
22. Very skilled person made money to some extent (5)
DEMON : Hidden in(… to some extent) “made money“.
Defn: … in a specific activity.
Lots to like here including SHEBANG for ‘matter’ at 1d, the parsing for AT THE HELM and the ARMADILLO (including your pic) at 14a.
No big deal, but for 23a I had WEN(T) reversed for ‘Endlessly travelled around’, which I think works better with ‘travel’ in the past tense, rather than WEN(D). I didn’t know anything about Bridget Riley, so missed the parsing of 20d. I take your point about the difference between ‘leaving nothing behind’ and dying INTESTATE FOR 3d.
Another of your pics looks very tempting, but C con C rather than a TOSTADA for me tonight.
Thanks to Gila and scchua
This was great fun, and I can’t argue with WordPlodder’s choice of top clues @1.
Although I also share the reservations about the inaccuracy of the definition for 3d, an important nuance for this clue is that “interstate” is also an Australian term. This is very neatly indicated by the use of “digger” rather than, for example, “car”.
Many thanks to Gila and to scchua.
Also had WENt for 23a. Agree that the definition in 3d doesn’t quite work.
My first stab at the anagram in 1a led to Steven Weirdo which, fortunately, guided me to the correct answer.
I thought the surfaces were beautifully crafted making the solve that much sweeter.
Needed a bit of help but enjoyed the ones I got, especially enjoyed TADA in 17d and HEHE in 16a both clues were very good in their entirety
Thanks to Gila and scchua
For some reason that I can’t account for, I’ve never done a Gila puzzle before – but I shall certainly be looking out for them from now on.
I really enjoyed this one, especially AT THE HELM, INTESTATE (despite the reservation), SEMI-DETACHED, ENLARGE and TWO-PART.
Many thanks to Gila and scchua.
What everyone else says – some lovely clues with a fair few smiles. He he, tada and op art, for good example. I had an unparsed and careless DOYEN at 22d for a while – the yen being money. Those hidden words are my absolute blind spot but I’m certainly not complaining – “to some extent” should surely have been enough of a shove in the right direction! Also had went for 23a. Missed the subtlety of digger at 3d, so thanks to Rabbit Dave @2. Thanks to Gila and to scchua for the illustrated blog. Very impressed how early some people get started of a locked down Sunday morning ?
I think I share both enjoyments and frustrations with the majority of posters so far. I cut Gila some slack re INTESTATE in that, the moment the solution occurred, I took ‘leaving nothing’ to mean ‘leaving no instructions’. I overlap with Eileen with ticks for AT THE HELM and SEMI-DETACHED and with WordPlodder for ARMADILLO and SHEBANG. I’m another fan of TADA and I also enjoyed ITALICS and the surface/anagram for PRECONDITION.
Thanks Gila and scchua
This was my most enjoyable puzzle of the week. Lovely wordplays and being a boater I appreciated the nautical references. Only quibble is that if you’re at the helm you’re at the back of the boat – can you lead from behind? Nevertheless a big thank you to Gila and scchua.
An excellent puzzle from Gila – very much enjoyed.
I went with WordPlodder and others with the parsing of 23a and thought RD made a good case for the Australian reference in 3d. I hadn’t heard of TED talks previously, obviously not that well-known to some of us!
My favourite was MAKE ENDS MEET, followed closely by SEMI-DETACHED & TOSTADA – the latter for the TADA!
Many thanks to Gila and to scchua for the review.
Apart from thinking that the extremists in MAKE ENDS MEET went a bit too far, I enjoyed this. PostMark does a good job of justifying INTESTATE. I’ve never really considered what a SHEBANG was before. Can you ever have one that isn’t whole? I congratulate Gila on finding with TED a new (to me, at least) way of cluing a past participle that all too often involves journalists.
Boatlady @ 8
[“Can you lead from behind?”
Boris Johnson does.
Or rather waits at the back to see where everyone’s going, then rushes to the front shouting “Follow me” (I forget whether it was Michael Heseltine or Max Hastings who said that).]