IE lets you play Silk from the Belgariad/Mallorean series by Eddings. Though arguably, Silk had a LOT of personas he used, not just one.

I would also contend that Assassin is one of the most selfish archetypes, in both senses of the word. They want to go first at the start of combat to get the drop on their foe, to the point where they'll ignore the party plan. And none of their subclass abilities are party facing. At best, you might end up with something like Blatant Beast describes, where the assassin is using their infiltration ability to play party leader and get the party into a base or something; but when used 'correctly', the ability is really about being part of an organization long term, where you might be able to get other party members hired A-Team style, but that really depends on the party make up more than the campaign, IMO. A Devotion Paladin will more than likely have a hard time getting accepted and being part of team evil. An Archfey Warlock will be sad trying to infiltrate Team TreeKiller to help the assassin 'take them out from the inside.'

In regards to advantage on checks to replicate IE with other Rogue archetypes, it reminds me of a time where a Rogue with a Cloak of the Elvenkind was trying to stealth up the stairs of a ziggurat to bypass a line of archers. Rolled two nat 1s and got peppered. It happens, and it doesn't even need to be nat 1s. Any two low rolls can happen and now you're either killed, or captured, or fighting a group you didn't want to (for whatever reason, otherwise why go the infiltration route?)

The funny thing to me, is all the various ways to play 'Spy' is grappling with the a playstyle 5E isn't built for. It runs smack dab into the Exploration and Social pillars with zero support for PCs that aren't built for it, very little support in the way of how to actually run intrigue at the DM level (especially when your players are playing classes that go against type). This is Dungeons and Dragons, not Bond (James) and Powers (Austin). As such, I'll throw my hat in the ring for those desiring a complete rebuild of the classes that actually fit the theme of game, rather than trying to shoehorn the other classes into a style the game doesn't support well.