Trailer #1

[will]

If they want to continue promoting the film primarily as a comedy, then they could show with Last Vegas.

I don't think second trailers need to be attached to another film of the same studio. But even if that were the case, I doubt they would wait for a new Paramount release.
I think they're at a stage now where the trailer needs to play all the time in front of all movies, except kids movies. They'll send it to theaters and it will be at the theater people's discretion to show it as much as they want.

[nas78]

‘Wolf of Wall Street’ Wins Trailer of the Year
blog.viacom.com/2013/11/wolf-of-wall-street-wins-trailer-of-the-year/

I’m not the only one excited to see Martin Scorsese’s Wolf of Wall Street this Christmas. The action packed trailer just won the 2013 Grand Key Art Award for audio/visual, the top honor at Hollywood Reporter’s Key Art Awards. This prominent awards competition, managed by the CLIO Awards, celebrates creative excellence and breakthrough concepts in entertainment advertising across film, television and gaming.
Paramount’s Wolf of Wall Street trailer teases the corporate greed story of New York stockbroker Jordan Belfort (Leonardo DiCaprio) to a pulsing track from Kanye West. The tempting trailer has it all from money, power, greed, women, cars, yachts, pool parties – fully living up to the motto that “more is never enough.”