Per Think with Google, 43 million viewers tuned in to the Oscars last year. Further, tens of millions of Oscar-related Google searches and tons of related YouTube content mean there are many opportunities for brands to participate in award events like Sunday’s telecast of the 87th Academy Awards.

In addition, Think with Google notes there are many more Oscar-related searches on YouTube and Google the day after an awards show and, further, videos about award shows are watched for months afterward.

“The Oscars in particular has a long shelf life, with interest picking back up in the fall,” according to Think with Google.

In other words, marketers have a huge window of opportunity to capitalize on award shows and serve up relevant content to continue to connect with consumers – even long after the event itself. Already, some brands have given us a preview of their Oscar plans.

According to Matthew Clyde, chief strategist and president at interactive agency Ideas Collide, live event programming like the Oscars or even the recent 40th anniversary SNL special help advertisers get more audience share and attention because there’s a live, engaged audience that is actually paying attention as opposed to more predictable scheduled programming that is consumable on mobile devices and on demand.

This also means brands that tie in a social component can further leverage their reach and share, he said.

However, challenges clearly remain, such as making the content and related consumer interaction authentic.

Here’s a look at four specific moments marketers have during awards shows and ways brands can seize them.

1. The Product Placement Moment

Clyde points to the Pharrell/Arby’s moment at the Grammys with the hat and the “very organic moment that became such a big sensation.”

“This year, however, everyone was trying to replicate that too much,” Clyde said. “It requires authenticity and smart, engaged marketers to know what the audience is going to see through. I think that’s the challenge of the marketing engine…there’s always now a constant content machine to feed and live events require marketers to be more on their toes than before.”

He points to hotel brand Hilton, which has been a longtime Grammys sponsor and tweeted to Pharrell about his bellboy outfit during the Grammys this year.

“I’m curious – was that strategically placed or luck that Hilton was a promotional sponsor of the Grammys and he wore that outfit?” Clyde said. “It’s like the Samsung thing [at the Oscars], too…product placement is more and more something major brands are having a think about. ‘What can we do to keep that live entertainment user talking and expressing more about our brands?’”

2. The Real-Time Moment

In fact, Clyde said brands and marketers now have to behave much more like live broadcasters of yore and produce in the moment.

“Gone are the days of creating campaigns over eight weeks and then launching,” Clyde said. “You also have to create content and visuals in the moment live as it is happening, like a broadcaster would be doing.”

Oreo’s Super Bowl tweet is a great example, but, again, the challenge is to find a natural fit, otherwise it’s just an interruption, Clyde said.

3. The Ready-for-Anything Moment

Another challenge is that the Oscars and other awards shows are “a little more of a wild card in terms of an event like a Super Bowl” because they “depend on the host or the movies up for nomination and actors popular at the time,” said Sarah Neal Simpson, associate director of mobile and social platforms at advertising agency R/GA.

Another barrier awards show advertisers face: “you never really have confirmation of what someone is going to wear [at an awards show] until the second before they step out,” Simpson said. “It’s hard to be real time…and it’s hard to plan for these things” when trying to also create context around celebrities and moments.

4. The Making-High-Glamour-Relatable Moment

Another obstacle for marketers is taking a highly glamorous awards show moment and making it relevant to an existing audience and potential consumers watching at home, Simpson said.

“I think what we’re seeing more and more of…in general, brands are trying to figure out how to make local invite-only real-time events relevant to the audience and speak to their brand messaging because I think traditional PR is fluctuating with social media,” Simpson said.

For example, L’Oreal used an activation tied to the Golden Globes to bring looks to women at home on Tumblr and Instagram with the help of influencers.

Brands are also embracing platforms and the vernacular on platforms – or more consumer-centric language to be more relatable as Samsung did with its selfie last year to “get in on that trend and be more culturally relevant,” Simpson said.