$\textbf{Question 1:}$ Here, I show all cup products in the positive degrees of the wedge of finitely many spheres$($of different dimensions$)$ vanishes.
Let $p_i\colon \Bbb S^{r_1}\lor \cdots\lor \Bbb S^{r_k}\to \Bbb S^{r_i}$ be the projections for $i=1,...,k$. We have the isomorphism $p^*_1\oplus \cdots\oplus p_k^*\colon H^n(\Bbb S^{r_1};R)\oplus\cdots \oplus H^n(\Bbb S^{r_k};R)\to H^n(\Bbb S^{r_1}\lor\cdots\lor \Bbb S^{r_k})$.
Consider the projections $g\colon \Bbb S^{r_1}\lor\cdots\lor\Bbb S^{r_k}\to \Bbb S^{r_i}\lor \Bbb S^{r_j}$ and $q_i,q_j\colon \Bbb S^{r_i}\lor \Bbb S^{r_j}\to \Bbb S^{r_i},\Bbb S^{r_j}$. So, $q_ig=p_i,q_jg=p_j$. Hence, for $r_i+r_j>0$ we have
$$p_i^*[\Bbb S^{r_i}]^*\smile p_j^*[\Bbb S^{r_j}]^*=g^*\big(q_i^*[\Bbb S^{r_i}]^*\smile q_j^*[\Bbb S^{r_j}]\big)$$$$\in g^*\big(H^{r_i+r_j}(\Bbb S^{r_i}\lor\Bbb S^{r_j})\big)=g^*\big(H^{r_i+r_j}(\Bbb S^{r_i})\oplus H^{r_i+r_j}(\Bbb S^{r_j})\big)=g^*(0\oplus 0)=0.$$
$\textbf{Product Theorem:}$ Let $(X,A)$ and $(Y,B)$ be pairs of topological spaces. Let $A_1,A_2\in \{\varnothing ,A\}$ and $B_1,B_2\in \{\varnothing, B\}$. Consider the projections $p,q\colon X\times Y\to X,Y$. Suppose, $(X\times Y,A\times Y,X\times B)$ is an excisive triad. Let $\alpha\in H^k(X,A_1),\ \beta\in H^l(Y,B_1), \mu\in H_{m-k}(X,A_2),\ \nu\in H_n(Y,B_1\cup B_2)$. Then, $$\big(p^*(\alpha)\smile q^*(\beta)\big)\frown (\mu\times \nu)=(-1)^{\deg \alpha\cdot \deg \beta\ +\ \deg \beta \cdot \deg \mu}(\alpha\frown \mu)\times (\beta\frown \nu)$$ in $H_{m+n-k-l}(X\times Y,X\times B_2\cup A_2\times Y)$.
$\textbf{Note:}$ Here $\times$ is the cross product, and the power of $-1$ may be different in different literature.
$\textbf{Fact:}$ Let $M,N$ be two connected compact oriented manifolds with the fundamental classes $[M]\in H_m(M,\partial M),\ [N]\in H_n(N,\partial N)$. Let $p,q\colon M\times N\to M,N$ be the projections. So, $p^*[M]^*\in H^m(M\times N,\partial M\times N),\ q^*[N]^*\in H^n(M\times N,M\times \partial N)$.
Now, for $x\in M,\ y\in N$ in $H_0(M\times N)$ we have$$\big(p^*[M]\smile q^*[N]\big)\frown [M\times N]=\big(p^*[M]^*\smile q^*[N]^*\big)\frown\big([M]\times [N]\big)$$$$=(-1)^{mn+mn}\big([M]^*\frown [M]\big)\times ([N]^*\frown [N]\big)=[x]\times [y]=\big[(x,y)\big]$$$$\implies p^*[M]^*\smile q^*[N]^*=[M\times N]^*.$$ Note that the fundamental class $[M\times N]\in H_{m+n}\big(M\times N, \partial(M\times N)\big)$ is same as the $[M]\times [N]$, this follows once you consider the isomorphism $$H_m(M,M\backslash x)\otimes H_n(N, N\backslash y)\xrightarrow[\cong]{\text{cross product}} H_{m+n}\big(M\times N,M\times N\backslash (x,y)\big)$$
$\textbf{Question 2:}$ Consider pojections $p,q\colon \Bbb S^p\times \Bbb S^q\to\Bbb S^p,\ \Bbb S^q$ to see $p^*[\Bbb S^p]^*\smile q^*[\Bbb S^q]^*=[\Bbb S^p\times \Bbb S^q]^*=$the dual fundamental class of the oriented $(p+q)$-dimensional manifold $\Bbb S^p\times \Bbb S^q$.
$\textbf{The Künneth Theorem for cohomology groups:}$ Let $X$ and $Y$
be two topological spaces. We denote by $p,q \colon X \times Y \to X,Y$ the projection maps. If all the homology groups of $X$ are finitely generated, then given any $n\geq 0$, there exists a short exact sequence
$$0\to \bigoplus_{k+l=n}H^k(X;\Bbb Z)\otimes H^l(Y;\Bbb Z)\xrightarrow{\times} H^n(X\times Y;\Bbb Z)$$$$\to \bigoplus_{k+l=n+1}\text{Tor }\big(H^k(X;\Bbb Z),H^l(Y;\Bbb Z)\big)\to 0 $$
which is natural with respect to the topological spaces $X$ and $Y$. If all the homology groups of $Y$ are also finitely generated, then the short exact sequence splits. The map $\times$ can be described considering $H^k(X;\Bbb Z)\otimes H^l(Y;\Bbb Z)\ni \varphi\otimes \psi\longmapsto p^*\varphi\smile q^*\psi\in H^{k+l}(X\times Y;\Bbb Z)$
$\textbf{Question 2:}$ One can also prove $p^*[\Bbb S^p]^*\smile q^*[\Bbb S^q]^*\neq 0$ considering the above, as for this particular case we have the isomorphism $$\Bbb Z\cong\Bbb Z\otimes \Bbb Z\cong H^p(\Bbb S^p;\Bbb Z)\otimes H^q(\Bbb S^q;\Bbb Z)\ni \varphi\otimes \psi\longmapsto p^*\varphi\smile q^*\psi\in H^{p+q}(\Bbb S^p\times \Bbb S^q;\Bbb Z)\cong \Bbb Z$$